Androgen receptor modulators and methods for use thereof

ABSTRACT

Compounds of structural formula (I) as herein defined are disclosed as useful in a method for modulating the androgen receptor in a tissue selective manner in a patient in need of such modulation, as well as in a method of agonizing the androgen receptor in a patient, and in particular the method wherein the androgen receptor is antagonized in the prostate of a male patient or in the uterus of a female patient and agonized in bone and/or muscle tissue. These compounds are useful in the treatment of conditions caused by androgen deficiency or which can be ameliorated by androgen administration, including: osteoporosis, periodontal disease, bone fracture, bone damage following bone reconstructive surgery, sarcopenia, frailty, aging skin, male hypogonadism, post-menopausal symptoms in women, atherosclerosis, hypercholesterolemia, hyperlipidemia, aplastic anemia and other hematopoietic disorders, pancreatic cancer, renal cancer, arthritis and joint repair, alone or in combination with other active agents. In addition, these compounds are useful as pharmaceutical composition ingredients alone and in combination with other active agents.

CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] The present application claims priority of U.S. provisionalapplication Serial No. 60/308,841, filed Jul. 31, 2001.

BACKGROUND OF THE INVENTION

[0002] Androgens play important roles in post-natal development that aremost pronounced at adrenarche and pubarche. Androgen production promotesthe musculoskeletal anabolism associated with the pubertal growth inboth males and females. At puberty, ovarian and testicular androgens areresponsible for pubertal hair, acne, and enhancement of libido. Inmales, exposure to 100-fold increased levels of endogenous androgensresults in the gender dimorphism in bone mass, muscle mass (positivenitrogen balance), and upper body strength, and are required for normalsexual development (genitalia, spermatogenesis, prostate and seminalvesicle maturation). Delay in puberty decreases the peak bone massachieved during adulthood. (Bhasin, S., et al., Eds. Pharmacology,Biology, and Clinical Applications of Androgens: Current Status andFuture Prospects. Wiley-Liss, Inc.:New York, 1996). In women, naturalmenopause causes virtually complete loss of ovarian estrogen productionand gradually reduces ovarian production of androgen by approximately50%. The physiological consequences of reduced androgen production aftermenopause are evident in decreased energy and libido, and contributesignificantly in many women to vasomotor symptoms. Decreased androgenoutput is also thought to contribute—along with declining pituitarygrowth hormone (GH) secretion and insulin derived growth factor 1 (IGF1)action—to age-dependent sarcopenia, negative nitrogen balance and lossof bone mass. (Vestergaard, et al., Effect of sex hormone replacement onthe insulin-like growth factor system and bone mineral: across-sectional and longitudinal study in 595 perimenopausal womenparticipating in the Danish Osteoporosis Prevention Study, J ClinEndocrinol Metab. 84:2286-90, 1999; and Bhasin, et al., Eds.Pharmacology, Biology, and Clinical Applications of Androgens: CurrentStatus and Future Prospects, Wiley-Liss, Inc.:New York. 1996).Postmenopausal osteoporosis results mainly from estrogen deficiency.However, many women who received estrogen replacement therapy still losebone with age and develop age—related osteoporotic fractures (albeit ata lower rate than those taking estrogens), indicating that bothestrogens and androgens play important roles for bone health in bothwomen and men. The simultaneous decreases in bone mass, muscle mass andmuscle strength increase the risk of falls and especially of hipfractures in both men and women >65 years of age. In fact, one-third ofall hip fractures occur in men.

[0003] The androgen receptor (AR) belongs to the nuclear receptorsuperfamily and controls transcription in a ligand dependent manner(Brinkman, et al., Mechanisms of androgen receptor activation andfunction, J. Ster. Biochem. Mol. Biol. 69, 307-313, 1999). Upon androgenbinding, AR binds directly to specific DNA sequences present in thepromoter region of androgen responsive genes, termed androgen responseelements (AREs), to stimulate transcription. Using ARE-dependenttranscription as a criterion, agents that bind to AR and stimulateARE-dependent transcription can be classified as agonists, and thosethat bind to AR and suppress ARE-dependent transcription are classifiedas antagonists. A number of natural or synthetic androgen agonists havebeen used for treatment of musculoskeletal or hematopoietic disordersand for hormone replacement therapy. In addition, AR antagonists, suchas flutamide or bicalutamide, are used for treatment of prostate cancer.However, clinical use of these androgen agonists or antagonists havebeen limited because of undesirable effects, such as hirsutism andprostate enlargement for agonists, and bone loss, fracture, gynecomastiaand sarcopenia for antagonists. It would be useful to have availableandrogens with tissue selective agonistic activity, which increase boneformation and muscle mass but do not induce the virilization.

[0004] Osteoporosis is characterized by bone loss, resulting from animbalance between bone resorption (destruction) and bone formation,which starts in the fourth decade continues throughout life at the rateof about 1-4% per year (Eastell, Treatment of postmenopausalosteoporosis, New Eng. J. Med. 338: 736, 1998). In the United States,there are currently about 20 million people with detectable fractures ofthe vertebrae due to osteoporosis. In addition, there are about 250,000hip fractures per year due to osteoporosis, associated with a 12%-20%mortality rate within the first two years, while 30% of patients requirenursing home care after the fracture and many never become fullyambulatory again. In postmenopausal women, estrogen deficiency leads toincreased bone resorption resulting in bone loss in the vertebrae ofaround 5% per year, immediately following menopause. Thus, first linetreatment/prevention of this condition is inhibition of bone resorptionby bisphosphonates, estrogens, selective estrogen receptor modulators(SERMs) and calcitonin. However, inhibitors of bone resorption are notsufficient to restore bone mass for patients who have already lost asignificant amount of bone. The increase in spinal BMD attained bybisphosphonate treatment can reach 11% after 7 years of treatment withalendronate. In addition, as the rate of bone turnover differs from siteto site; higher in the trabecular bone of the vertebrae than in thecortex of the long bones, the bone resorption inhibitors are lesseffective in increasing hip BMD and preventing hip fracture. Therefore,osteoanabolic agents, which increase cortical/periosteal bone formationand bone mass of long bones, would address an unmet need in thetreatment of osteoporosis especially for patients with high risk of hipfractures. The osteoanabolic agents also complement the bone resorptioninhibitors that target the trabecular envelope, leading to abiomechanically favorable bone structure. (Schmidt, et al., Anabolicsteroid: Steroid effects on bone in women, 1996, In: J. P. Bilezikian,et al., Ed. Principles of Bone Biology. San Diego: Academic Press.)

[0005] A number of studies provide the proof of principle that androgensare osteoanabolic in women and men. Anabolic steroids, such asnandrolone decanoate or stanozolol, have been shown to increase bonemass in postmenopausal women. Beneficial effects of androgens on bone inpost-menopausal osteoporosis are well-documented in recent studies usingcombined testosterone and estrogen administration (Hofbauer, et al.,Androgen effects on bone metabolism: recent progress and controversies,Eur. J. Endocrinol. 140, 271-286, 1999). Combined treatment increasedsignificantly the rate and extent of the rise in BMD (lumbar and hip),relative to treatment with estrogen alone. Additionally,estrogen—progestin combinations that incorporate an androgenic progestin(norethindrone) rather than medroxyprogesterone acetate yielded greaterimprovements in hip BMD. These results have recently been confirmed in alarger (N=311) 2 year, double blind comparison study in which oralconjugated estrogen (CEE) and methyltestosterone combinations weredemonstrated to be effective in promoting accrual of bone mass in thespine and hip, while conjugated estrogen therapy alone prevented boneloss (A two-year, double-blind comparison of estrogen-androgen andconjugated estrogens in surgically menopausal women: Effects on bonemineral density, symptoms and lipid profiles. J Reprod Med.44(12):1012-20, 1999). Despite the beneficial effects of androgens inpostmenopausal women, the use of androgens has been limited because ofthe undesirable virilizing and metabolic action of androgens. The datafrom Watts and colleagues demonstrate that hot flushes decrease in womentreated with CEE+ methyltestosterone; however, 30% of these womensuffered from significant increases in acne and facial hair, acomplication of all current androgen pharmacotherapies (Watts, et al.,Comparison of oral estrogens and estrogens plus androgen on bone mineraldensity, menopausal symptoms, and lipid-lipoprotein profiles in surgicalmenopause, Obstet. Gynecol. 85, 529-537, 1995). Moreover, the additionof methyltestosterone to CEE markedly decreased HDL levels, as seen inother studies. Thus, the current virilizing and metabolic side effectprofile of androgen therapies provide a strong rationale for developingtissue selective androgen agonists for bone.

[0006] It is well established that androgens play an important role inbone metabolism in men, which parallels the role of estrogens in women.(Anderson, et al., Androgen supplementation in eugonadal men withosteoporosis—effects of 6 months of treatment on bone mineral densityand cardiovascular risk factors, Bone 18: 171-177, 1996). Even ineugonadal men with established osteoporosis, the therapeutic response totestosterone treatment provides additional evidence that androgens exertimportant osteoanabolic effects. Mean lumbar BMD increased from 0.799gm/cm² to 0.839 g/cm², in 5 to 6 months in response to 250 mg oftestosterone ester IM q fortnight (p=0.001). A common scenario forandrogen deficiency occurs in men with stage D prostate cancer(metastatic) who undergo androgen deprivation therapy (ADT). Endocrineorchiectomy is achieved by long acting GnRH agonists, while androgenreceptor blockade is implemented with flutamide or bicalutamide (ARantagonists). In response to hormonal deprivation, these men suffer fromhot flushes, significant bone loss, weakness, and fatigue. In a recentpilot study of men with stage D prostate cancer, osteopenia (50% vs.38%) and osteoporosis (38% vs. 25%) were more common in men who hadundergone ADT for >1 yr than the patients who did not undergo ADT (Wei,et al. Androgen deprivation therapy for prostate cancer results insignificant loss of bone density, Urology 54: 607-11, 1999). Lumbarspine BMD was significantly lower in men who had undergone ADT(P=0.008). Thus, in addition to the use of tissue selective AR agonistsfor osteoporosis, tissue selective AR antagonists in the prostate thatlack antagonistic action in bone and muscle may be a useful treatmentfor prostate cancer, either alone or as an adjunct to traditional ADTsuch as GnRH agonist/antagonist. (See also Stoche, et al., J Clin.Endocrin. Metab. 86:2787-91, 2001).

[0007] Additionally, it has been reported that patients with pancreaticcancer treated with the antiandrogen flutamide have been found to haveincreased survival time. (Greenway, B. A., Drugs & Aging, 17(3), 161,2000). The tissue selective androgen receptor modulators of the presentinvention may be employed for treatment of pancreatic cancer, eitheralone or as an adjunct to treatment with an antiandrogen.

[0008] The possibility of tissue selective AR agonism was suggested byandrogen insensitivity syndrome (AIS), which results from mutations inAR gene located at X chromosome. (Quigley, et al., Androgen receptordefects: Historical, clinical, and molecular perspectives. EndocrineReviews. 16:546-546, 1995). These mutations cause different degrees ofandrogen insensitivity. While complete lack of androgen responsivenessdevelops as a female phenotype with female-type bones, subtle mutations(one amino acid substitution) of AR may lead to partial AIS withdifferent degrees of abnormality in male sexual development often withmale-type skeleton. A similar aberration in male sex organ developmentis also found in individuals with mutations in 5α-reductase type 2 gene,that converts testosterone to 5α-dihydro-testosterone (5α-DHT)(Mendonca, et al., Male pseudohermaphroditism due to steroid5alpha-reductase 2 deficiency: Diagnosis, psychological evaluation, andmanagement, Medicine (Baltimore), 75:64-76 (1996)). These patientsexhibit partial development of male organs with normal male skeleton,indicating that testosterone cannot substitute for 5α-DHT as anactivator of AR in genital development. This ligand specificity forcertain tissues raises the possibility that androgenic compounds with ARagonistic activity could have specificity for certain tissues, such asbone, while lacking activity in other tissues, such as those responsiblefor virilization.

[0009] Recent advances in the steroid hormone receptor field uncoveredthe complex nature of transcription controlled by AR and other nuclearreceptors (Brinkman, et al., Mechanisms of androgen receptor activationand function, J. Ster. Biochem. Mol. Biol. 69:307-313 1999). Uponbinding to ARE as a homo-dimer, agonist-bound AR stimulatestranscription by recruiting a large enzymatic co-activator complex thatincludes GRIP1/TIF2, CBP/p300 and other coactivators. Transcriptionalactivities of AR have been functionally mapped to both the N-terminaldomain (NTD) and C-terminal ligand binding domain (LBD), also termedactivation function AF1 and AF2, respectively. A feature of AR is theligand mediated interaction of AR NTD with LBD (N—C interaction) whichis essential for most ligand induced transcriptional activation. Inaddition, agonist-bound AR can also suppress transcription viaprotein-protein interaction with transcription factor complexes such asAP1, NFκB and Ets family. Both AR agonist-induced transcriptionalactivation and repression are context (cell type and promoter) dependentand are reversed by AR antagonists, providing the possibility forligand-dependent, context specific agonism/antagonism. Androgenicligands, thus, may lead to tissue selective AR agonism or partial ARagonism/antagonism, and have been named selective AR modulators (SARMs).

[0010] What is needed in the art are compounds that can produce the samepositive responses as androgen replacement therapy without the undesiredside effects. Also needed are androgenic compounds that exert selectiveeffects on different tissues of the body. In this invention, wedeveloped a method to identify SARMs using a series of in vitrocell-assays that profiles ligand mediated activation of AR, such as (i)N—C interaction, (ii) transcriptional repression, (iii) transcriptionalactivation dependent on AF1 or AF2 or native form of AR. SARM compoundsin this invention, identified with the methods listed above, exhibittissue selective AR agonism in vivo, i.e. agonism in bone (stimulationof bone formation in rodent model of osteoporosis) and antagonism inprostate (minimal effects on prostate growth in castrated rodents andantagonism of prostate growth induced by AR agonists). Such compoundsare ideal for treatment of osteoporosis in women and men as amonotherapy or in combination with inhibitors of bone resorption, suchas bisphosphonates, estrogens, SERMs, cathepsin K inhibitors, αVβ3antagonists, calcitonin, proton pump inhibitors. SARM compounds may alsobe employed for treatment of prostate disease, such as prostate cancerand benign prostate hyperplasia (BPH). Moreover, compounds in thisinvention exhibit minimal effects on skin (acne and facial hair growth)and can be used for treatment of hirsutism. Additionally, compounds inthis invention can exhibit muscle growth and can be used for treatmentof sarcopenia and frailty. Moreover, compounds in this invention canexhibit androgen agonism in the central nervous system and can be usedto treat vasomotor symptoms (hot flush) and can increase energy andlibido, particularly in post-menopausal women. The compounds of thepresent invention may be used in the treatment of prostate cancer,either alone or as an adjunct to traditional GnRH agonist/antagonisttherapy for their ability to restore bone, or as a replacement forantiandrogen therapy because of the ability to antagonize androgen inthe prostate, and minimize bone depletion in the skeletal system.Further, the compounds of the present invention may be used for theirability to restore bone in the treatment of pancreatic cancer as anadjunct to treatment with antiandrogen, or as solo agents for theirantiandrogenic properties, offering the advantage over traditionalantiandrogens of being bone-sparing. Additionally, compounds in thisinvention can increase the number of blood cells, such as red bloodcells and platelets and can be used for treatment of hematopoieticdisorders such as aplastic anemia. Finally, compounds in this inventionhave minimal effects on lipid metabolism, thus considering their tissueselective androgen agonism listed above, the compounds in this inventionare ideal for hormone replacement therapy in hypogonadic (androgendeficient) men.

[0011] Substituted 4-aza-5α-androst-1-en-3-one-17β-carboxamides aredisclosed as inhibitors of the enzyme 5α-reductase and useful fortreating hyperandrogenic conditions in U.S. Pat. Nos. 4,377,584;4,760,071; 5,116,983; 5,693,809; 5,696,266; 5,872,126; 5,547,957;5,693,810; 6,001,844; 6,121,449; 6,147,213; 5,302,621; as well as WO92/16213; WO 92/16233; WO 92/18132; WO 94/14452; WO 94/15602; WO94/11385; WO 95/10284; WO 95/07926; WO 94/03474; WO 95/07926; WO97/10217; WO 97/11702; WO 00/18402; WO 99/35161; EP 0 538 192; EP 0 298652; EP 0 004 949; EP 0 428 366; EP 0 367 502; EP 0 655 459; and EP 0484 094. Rasmusson, et al. “Azasteroids as Inhibitors of Rat Prostatic5α-Reductase”, J. Med. Chem. 27: 1690 (1984); Rasmusson, et al.,“Azasteroids: Structure-Activity Relationships for Inhibition of5α-Reductase and of Androgen Receptor Binding” J. Med. Chem. 29(11):2298 (1986); Bakshi, et al.“4-aza-3-oxo-5α-androst-1-ene-17β-N-aryl-carboxamides as Dual Inhibitorsof Human Type 1 and Type 2 Steroid 5α-Reductases. Dramatic Effect ofN-Aryl Substituents on Type 1 and Type 2 5α-Reductase InhibitoryPotency” J. Med. Chem. 38(17): 3189 (1995) also disclose substituted4-aza-5α-androst-1-en-3-one-17β-carboxamides. Substituted4-aza-5α-androstan-3-one-17β-carboxamides are disclosed in U.S. Pat. No.5,817,802.

[0012] Tolman, et al.,“4-Methyl-3-oxo-4-aza-5α-androst-1-ene-17β-N-aryl-carboxamides: AnApproach to Combined Androgen Blockade 5α-Reductase Inhibition withAndrogen Receptor Binding In Vitro”, J. Steroid Biochem. Molec. Biol.60(5-6): 303 (1997), discloses that 4-N-methyl substitution andunsaturation of the A ring at the 1-2 position of4-aza-5α-androstan-3-one 17β-carboxamide 5α-reductase type 2 inhibitorsincreased androgen receptor affinity and that N-aryl substitution at the17-carboxamide increased affinity for the type 1 isozyme of5α-reductase. Tolman, et al., posit that these compounds will haveutility in the treatment of prostatic carcinoma and will providecomplete androgen blockade. The following compounds are disclosed,together with their IC50s for the type 1 and type 2 5α-reductase enzymeand for the human androgen receptor.

[0013] wherein R is H, 2-methyl, 2-methoxy, 2-chloro, 4-chloro,2-fluoro, 2-trifluoromethyl, and 2,5-bis-trifluromethyl.

[0014] PCT publications WO 98/25623 and WO 98/25622 are directed to theuse of the 5α-reductase inhibitors finasteride and17-alkyl-4-aza-5α-androstan-3-ones, respectively, as anti-resorptiveagents useful in the prevention and treatment of bone loss, as well asprevention and treatment of osteoporosis and osteopenia and otherdiseases where inhibiting bone loss may be beneficial, including:Paget's disease, malignant hypercalcemia, periodontal disease, jointloosening and metastatic bone disease, as well as reducing the risk offractures, both vertebral and nonvertebral. In the treatment ofosteoporosis, the activity of bone resorption inhibitors is distinctfrom the activity of tissue selective androgen receptor modulators(SARMs). Rather than inhibiting bone resorption, the SARMs of thepresent invention stimulate bone formation, acting preferentially oncortical bone, which is responsible for a significant part of bonestrength. Bone resorption inhibitors, in contrast, act preferentially ontrabecular bone.

SUMMARY OF THE INVENTION

[0015] Compounds of structural formula (I) as herein defined aredisclosed as useful in a method for modulating the androgen receptor ina tissue selective manner in a patient in need of such modulation, aswell as in a method of agonizing the androgen receptor in a patient, andin particular the method wherein the androgen receptor is agonized inbone and/or muscle tissue and antagonized in the prostate of a malepatient or in the uterus of a female patient. These compounds are usefulin the treatment of conditions caused by androgen deficiency or whichcan be ameliorated by androgen administration, including: osteoporosis,periodontal disease, bone fracture, bone damage following bonereconstructive surgery, sarcopenia, frailty, aging skin, malehypogonadism, post-menopausal symptoms in women, atherosclerosis,hypercholesterolemia, hyperlipidemia, aplastic anemia and otherhematopoietic disorders, pancreatic cancer, renal cancer, arthritis andjoint repair, alone or in combination with other active agents. Inparticular, the comopunds of the present invention are useful intreating glucocorticoid-induced osteoporosis. In addition, thesecompounds are useful as pharmaceutical composition ingredients alone andin combination with other active agents.

DETAILED DESCRIPTION OF THE INVENTION

[0016] The present invention relates to compounds useful as tissueselective androgen receptor modulators (SARMs).

[0017] Compounds of the present invention, which may be prepared inaccordance with the methods described herein, have been found to betissue selective modulators of the androgen receptor (SARMs). In oneaspect, compounds of the present invention may be useful to agonize theandrogen receptor in a patient, and in particular to agonize theandrogen receptor in bone and/or muscle tissue and antagonize theandrogen receptor in the prostate of a male patient or in the uterus ofa female patient and agonize the androgen receptor in bone and/or muscletissue. In another aspect of the present invention, compounds ofstructural formula I may be useful to agonize the androgen receptor inbone and/or muscle tissue and antagonize the androgen receptor in theprostate of a male patient or in the uterus or skin of a female patient.The agonism in bone can be assayed through stimulation of bone formationin the rodent model of osteoporosis, and the antagonism in the prostatecan be assayed through observation of minimal effects on prostate growthin castrated rodents and antagonism of prostate growth induced by ARagonists, as detailed in the Examples.

[0018] Yet another aspect of the present invention is a method toidentify SARMs using a series of in vitro cell-based assays. In thefirst of these series of assays (which may in practice be performed inany order), agonists of the androgen receptor (AR) are characterized bymeasuring Rhesus AR-dependent suppression of the human MMP-1 promoter inHEP G-2 cells transiently transfected with MMP1/luciferase promoter andthe Rhesus AR (RhAR). (Schneikert, et al., Androgen receptor-Ets proteininteraction is a novel mechanism for steroid hormone-mediateddown-modulation of matrix metalloproteinase expression, J Biol Chem. Sep27:271(39):23907-13, 1996. In this instance, the Rhesus AR mediatesligand-dependent promoter suppression of the MMP1 promoter viaprotein-protein interactions with uncharacterized factors bound to theEts cognate. SARMs display agonist activity in this assay by repressingtranscription. A compound's in vivo viralizing potential, mediatedthrough the AR, is reflected in vitro by its ability to stably assemblean AR N-terminal/C-terminal interaction. (He, et al., Activationfunction in the human androgen receptor ligand binding domain mediatesinterdomain communication with the NH(2)-terminal domain. J Biol Chem.274: 37219 1999). Two transcription assays have been developed to screenfor compounds with reduced potential to induce virilizing effects invivo. In the first transcription assay, the in vivo virilizing potentialmediated by activated androgen receptors is reflected in the capacity ofrhAR ligands to induce the N-terminal/C-terminal interaction in amammalian 2-hybrid assay in CV-1 monkey kidney cells. SARMs display weakor no agonist activity in this assay. In the second transcription assay,the same test compound is assayed in the same format in the presence ofa full virilizing androgen agonist and the capacity of the compound toantagonize the stimulation induced by the full androgen agonist isquantified. SARMs of the present invention display antagonist activityin in this assay.

[0019] In a further aspect of the present invention are compounds ofstructural formula I that antagonize the androgen receptor in theprostate of a male patient or in the uterus of a female patient, but notin hair-growing skin or vocal cords, and agonize the androgen receptorin bone and/or muscle tissue, but not in organs which control bloodlipid levels (e.g. liver). These compounds are useful in the treatmentof conditions caused by androgen deficiency or which can be amelioratedby androgen administration, including: osteoporosis, periodontaldisease, bone fracture, bone damage following bone reconstructivesurgery, sarcopenia, frailty, aging skin, male hypogonadism,post-menopausal symptoms in women, atherosclerosis,hypercholesterolemia, hyperlipidemia, aplastic anemia and otherhematopoietic disorders, arthritis and joint repair, alone or incombination with other active agents. In addition, these compounds areuseful as pharmaceutical composition ingredients alone and incombination with other active agents.

[0020] The compounds of the present invention may be used to treatconditions which are caused by androgen deficiency or which can beameliorated by androgen administration, including, but not limited to:osteoporosis, periodontal disease, bone fracture, bone damage followingbone reconstructive surgery, sarcopenia, frailty, aging skin, malehypogonadism, post-menopausal symptoms in women, atherosclerosis,hypercholesterolemia, hyperlipidemia, aplastic anemia and otherhematopoietic disorders, arthritis and joint repair, alone or incombination with other active agents. Treatment is effected byadministration of a therapeutically effective amount of the compound ofstructural formula I to the patient in need of such treatment.

[0021] The compounds of structural formula I may also be employed asadjuncts to traditional androgen depletion therapy in the treatment ofprostate cancer to restore bone, minimize bone loss, and maintain bonemineral density. In this manner, they may be employed together withtraditional androgen deprivation therapy, including GnRHagonists/antagonists such as leuprolide. It is also possible that thecompounds of structural formula I may be used in combination withantiandrogens such as flutamide, hydroxy-flutamide (the active form offlutamide), and Casodex™ (the trademark for ICI 176,334 from ImperialChemical Industries PLC, presently Astra-Zeneca) in the treatment ofprostate cancer.

[0022] Further, the compounds of the present invention may also beemployed in the treatment of pancreatic cancer, either for theirandrogen antagonist properties or as an adjunct to an antiandrogen suchas flutamide, hydroxy-flutamide (the active form of flutamide), andCasodex™ (the trademark for ICI 176,334).

[0023] Compounds of structural formula I have minimal negative effectson lipid metabolism, thus considering their tissue selective androgenagonism listed above, the compounds in this invention are ideal forhormone replacement therapy in hypogonadic (androgen deficient) men.

[0024] Additionally, compounds in this invention can increase the numberof blood cells, such as red blood cells and platelets and can be usedfor treatment of hematopoietic disorders such as aplastic anemia.

[0025] Compounds of the present invention are described by the followingchemical formula I:

[0026] wherein:

[0027] “a” and “b” are independently selected from a single bond and adouble bond;

[0028] R¹ is selected from:

[0029] (1) C₁₋₃ alkyl,

[0030] (2) C₂₋₃ alkenyl,

[0031] (3) C₃₋₆ cycloalkyl,

[0032] (4) C₁₋₃ alkyl wherein one or more of the hydrogen atoms has beenreplaced with a fluorine atom,

[0033] (5) aryl, and

[0034] (6) aryl-C₁₋₃ alkyl;

[0035] R² is selected from:

[0036] (1) aryl, either unsubstituted or substituted,

[0037] (2) C₁₋₈ alkyl, unsubstituted or substituted,

[0038] (3) perfluoroC₁₋₈ alkyl,

[0039] (4) C₂₋₈ alkenyl, unsubstituted or substituted,

[0040] (5) C₃₋₈ cycloalkyl, either unsubstituted or substituted, and

[0041] (6) cycloheteroalkyl, unsubstituted or substituted;

[0042] R³ is selected from H and C₁₋₈ alkyl, or R² and R³, together withthe nitrogen atom to which they are attached, form a 5- to 7-memberedheterocyclic ring, optionally containing one or two additionalheteroatoms selected from N, S, and O, optionally having one or moredegrees of unsaturation, optionally fused to a 6-membered heteroaromaticor aromatic ring, either unsubstituted or substituted;

[0043] R⁴ and R⁵ are each independently selected from

[0044] (1) hydrogen,

[0045] (2) halogen,

[0046] (3) aryl,

[0047] (4) C₁₋₈ alkyl,

[0048] (5) C₃₋₈ cycloalkyl,

[0049] (6) C₃₋₈ cycloheteroalkyl,

[0050] (7) aryl C₁₋₆alkyl,

[0051] (8) amino C₀₋₆alkyl,

[0052] (9) C₁₋₆ alkylamino C₀₋₆alkyl,

[0053] (10) (C₁₋₆ alkyl)₂amino C₀₋₆alkyl,

[0054] (11) aryl C₀₋₆ alkylamino C₀₋₆alkyl,

[0055] (12) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl,

[0056] (13) C₁₋₆ alkylthio,

[0057] (14) aryl C₀₋₆alkylthio,

[0058] (15) C₁₋₆ alkylsulfinyl,

[0059] (16) aryl C₀₋₆alkylsulfinyl,

[0060] (17) C₁₋₆ alkylsulfonyl,

[0061] (18) aryl C₀₋₆alkylsulfonyl,

[0062] (19) C₁₋₆ alkoxy C₀₋₆alkyl,

[0063] (20) aryl C₀₋₆ alkoxy C₀₋₆alkyl,

[0064] (21) hydroxycarbonyl C₀₋₆alkyl,

[0065] (22) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl,

[0066] (23) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl,

[0067] (24) hydroxycarbonyl C₁₋₆ alkyloxy,

[0068] (25) hydroxy C₀₋₆alkyl,

[0069] (26) cyano,

[0070] (27) nitro,

[0071] (28) perfluoroC₁₋₄alkyl,

[0072] (29) perfluoroC₁₋₄alkoxy,

[0073] (30) C₀₋₆ alkylcarbonyl,

[0074] (31) C₁₋₆ alkylcarbonyloxy,

[0075] (32) aryl C₀₋₆alkylcarbonyloxy,

[0076] (33) C₁₋₆ alkylcarbonylamino,

[0077] (34) aryl C₀₋₆ alkylcarbonylamino,

[0078] (35) C₁₋₆ alkylsulfonylamino,

[0079] (36) aryl C₁₋₆alkylsulfonylamino,

[0080] (37) C₁₋₆ alkoxycarbonylamino,

[0081] (38) aryl C₀₋₆ alkoxycarbonylamino,

[0082] (39) C₁₋₆alkylaminocarbonylamino,

[0083] (40) aryl C₁₋₆alkylaminocarbonylamino,

[0084] (41) (C₁₋₆alkyl)₂ aminocarbonylamino,

[0085] (42) (aryl C₀₋₆alkyl)₂ aminocarbonylamino,

[0086] (43) (C₁₋₆alkyl)₂ aminocarbonyloxy,

[0087] (44) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, and

[0088] (45) spiro-C₃₋₈cycloalkyl;

[0089] or, R⁴ and R⁵ together form an oxo group or ═CH—R⁶ or a spiroC₃₋₇ cycloalkyl ring, unsubstituted or substituted with R⁶;

[0090] R⁶ is selected from:

[0091] (1) hydrogen, and

[0092] (2) C₁₋₄ alkyl;

[0093] or a pharmaceutically acceptable salt thereof.

[0094] In one embodiment of the present invention, “b” is a single bond.In one class of this embodiment, “b” is a single bond, and “a” is adouble bond. In another class of this embodiment, “b” is a single bond,and “a” is a single bond.

[0095] In another embodiment of the present invention, “b” is a doublebond. In one class of this embodiment, “b” is a double bond, and “a” isa double bond. In another class of this embodiment, “b” is a doublebond, and “a” is a single bond.

[0096] In one embodiment of the present invention, R¹ is selected from:

[0097] (1) C₁₋₃ alkyl,

[0098] (2) C₂₋₃ alkenyl,

[0099] (3) C₃₋₆ cycloalkyl,

[0100] (4) trifluoromethyl,

[0101] (5) aryl, and

[0102] (6) aryl-C₁₋₃ alkyl.

[0103] In another embodiment of the present invention R¹ is selectedfrom:

[0104] (1) C₁₋₃ alkyl,

[0105] (2) C₂₋₃ alkenyl,

[0106] (3) C₃₋₆ cycloalkyl, and

[0107] (4) trifluoromethyl.

[0108] In still another embodiment of the present invention R¹ isselected from:

[0109] (1) C₁₋₂ alkyl,

[0110] (2) C₃₋₆ cycloalkyl, and

[0111] (3) trifluoromethyl.

[0112] In yet another embodiment of the present invention R¹ is selectedfrom:

[0113] (1) methyl,

[0114] (2) cyclopropyl, and

[0115] (3) trifluoromethyl.

[0116] In one class of this embodiment, R¹ is selected from methyl andcyclopropyl. In a subclass of this embodiment R¹ is methyl.

[0117] In one embodiment of the present invention, R² is aryl, eitherunsubstituted or substituted with one to three substituents selectedfrom:

[0118] (a) halogen,

[0119] (b) aryl,

[0120] (c) C₁₋₈ alkyl,

[0121] (d) C₃₋₈ cycloalkyl,

[0122] (e) C₃₋₈ cycloheteroalkyl,

[0123] (f) aryl C₁₋₆alkyl,

[0124] (g) amino C₀₋₆alkyl,

[0125] (h) C₁₋₆ alkylamino C₀₋₆alkyl,

[0126] (i) (C₁₋₆ alkyl)₂amino C₀₋₆alkyl,

[0127] (j) aryl C₀₋₆ amino C₀₋₆alkyl,

[0128] (k) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl,

[0129] (l) C₁₋₆ alkylthio,

[0130] (m) aryl C₀₋₆alkylthio,

[0131] (n) C₁₋₆ alkylsulfinyl,

[0132] (o) aryl C₀₋₆alkylsulfinyl,

[0133] (p) C₁₋₆ alkylsulfonyl,

[0134] (q) aryl C₀₋₆alkylsulfonyl,

[0135] (r) C₁₋₆ alkoxy C₀₋₆alkyl,

[0136] (s) aryl C₀₋₆ alkoxy C₀₋₆alkyl,

[0137] (t) hydroxycarbonyl C₀₋₆alkyl,

[0138] (u) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl,

[0139] (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl,

[0140] (w) hydroxycarbonyl C₁₋₆ alkyloxy,

[0141] (x) hydroxy C₀₋₆alkyl,

[0142] (y) cyano,

[0143] (z) nitro,

[0144] (aa) perfluoroC₁ ₄alkyl,

[0145] (bb) perfluoroC₁₋₄alkyloxy,

[0146] (cc) oxo,

[0147] (dd) C₁₋₆ alkylcarbonyloxy,

[0148] (ee) aryl C₀₋₆alkylcarbonyloxy,

[0149] (ff) C₁₋₆ alkylcarbonylamino,

[0150] (gg) aryl C₀₋₆ alkylcarbonylamino,

[0151] (hh) C₁₋₆ alkylsulfonylamino,

[0152] (ii) aryl C₀₋₆alkylsulfonylamino,

[0153] (jj) C₁₋₆ alkoxycarbonylamino,

[0154] (kk) aryl C₀₋₆ alkoxycarbonylamino,

[0155] (ll) C₁₋₆alkylaminocarbonylamino,

[0156] (mm) aryl C₀₋₆alkylaminocarbonylamino,

[0157] (nn) (C₁₋₆alkyl)₂ aminocarbonylamino,

[0158] (oo) (aryl C₀₋₆alkyl)₂ aminocarbonylamino,

[0159] (pp) (C₁₋₆alkyl)₂ aminocarbonyloxy,

[0160] (qq) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy,

[0161] (rr) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and

[0162] (ss) aryl C₀₋₆ alkylcarbonyl C₀₋₆ alkyl;

[0163] In a class of this embodiment of the present invention, R² isaryl, substituted with one to three substituents selected from:

[0164] (a) halogen,

[0165] (b) aryl,

[0166] (c) C₁₋₆ alkyl,

[0167] (d) C₃₋₈ cycloheteroalkyl,

[0168] (e) benzyl,

[0169] (f) amino,

[0170] (g) C₁₋₆ alkylamino,

[0171] (h) C₁₋₆ alkylthio,

[0172] (i) C₁₋₆ alkoxy,

[0173] (j) hydroxy,

[0174] (k) cyano,

[0175] (l) nitro,

[0176] (m) perfluoroC₁₋₄alkyl,

[0177] (n) trifluoromethoxy,

[0178] (o) oxo,

[0179] (p) methylcarbonyloxy,

[0180] (q) methylcarbonylamino,

[0181] (r) methylsulfonylamino,

[0182] (s) methoxycarbonylamino,

[0183] (t) methylaminocarbonylamino,

[0184] (u) dimethylaminocarbonylamino, and

[0185] (v) dimethylaminocarbonyloxy.

[0186] In a subclass of this embodiment of the present invention, R² isaryl, substituted by one to three substituents selected from:

[0187] (a) halogen,

[0188] (b) aryl,

[0189] (c) C₁₋₆ alkyl,

[0190] (d) C₁₋₆ alkoxy,

[0191] (e) hydroxy,

[0192] (f) cyano,

[0193] (g) perfluoroC₁₋₄alkyl, and

[0194] (h) trifluoromethoxy,

[0195] In another subclass of this class of the present invention, R² isaryl, substituted by one to three substituents selected from:

[0196] (a) fluoro,

[0197] (b) chloro,

[0198] (c) bromo,

[0199] (d) phenyl,

[0200] (e) methyl,

[0201] (f) ethyl,

[0202] (g) benzyl,

[0203] (h) amino,

[0204] (i) cyano,

[0205] (j) morpholinyl,

[0206] (k) nitro,

[0207] (l) methoxy,

[0208] (m) methylthio,

[0209] (n) hydroxy,

[0210] (o) trifluoromethyl,

[0211] (p) trifluoromethoxy,

[0212] (q) formyl,

[0213] (r) acetyl, and

[0214] (s) oxo.

[0215] In one embodiment of the present invention, R² is selected fromphenyl, naphthyl, pyridyl, pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl,imidazolyl, benzimidazolyl, benzthiazolyl, benzoxazolyl, indolyl,thienyl, furyl, dihydrobenzofuryl, benzo(1,3)dioxolanyl,benzo(1,4)dioxanyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,indanyl, isoquinolinyl, dihydroisoquinolinyl, tetrahydronaphthyridinyl,benzothienyl, imidazopyridinyl, tetrahydrobenzazepinyl, quinoxalinyl,imidazopyrimidinyl, cyclopentenopyridinyl, phthalazinyl,tetrahydroquinolinyl, oxindolyl, isoquinolinyl, imidazothiazolyl,dihydroimidazothiazolyl, tetrazolyl, triazolyl, pyridazinyl,piperidinyl, piperazinyl, oxadiazolyl, thiadiazolyl, triazinyl,indazolyl, indazolinone, dihydrobenzofuranyl, phthalide, phthalimide,coumarin, chromone, tetrahydroisoquindine, naphthyridinyl,tetrahydronaphthyridinyl, isoindolinyl, triazanaphthalinyl, pteridinyl,purinyl, andquinolinyl. In one class of the present invention, R² isselected from: phenyl, quinolinyl, pyridyl, pyrazolyl, benzamidazolyl,imidazolyl, furyl, napthyl, indanyl, thienyl, pyrazinyl, benzothienyl,3,4-dihydro-1(1H)-isoquinolinyl, 1-8-tetrahydronaphthyridinyl,imidazo[1,2-a]pyridinyl, 2-oxo-2,3,4,5-tetrahydro-1H -benzo[B]azepinyl,quinoxalinyl, imidazo[1,2-a]pyrimidinyl, 2-3-cyclopentenopyridinyl,1-(2H)-phthalazinyl, 1,2,3,4-tetrahydroquinolinyl, oxindolyl,isoquinolinyl, imidazo[2,1-b][1,3]thiazolyl,2,3-dihydroimidazo[2,1-b][1,3]thiazolyl and indolyl. In a subclass ofthis class of the invention, R² is selected from phenyl, naphthyl,pyridyl, thienyl, pyrazinyl, and quinolinyl. In another subclass, R² isphenyl. In another class of this invention, R² is a bicyclic systemselected from: benzothienyl, 3,4-dihydro-1(1H)-isoquinolinyl,1-8-tetrahydronaphthyridinyl, imidazo[1,2a]pyridine,2-oxo-2,3,4,5-tetrahydro-1H-benzo[B]azepinyl, quinoxalinyl,imidazo[1,2a]pyrimidinyl, 2,3-cyclopentenopyridinyl, 1(2H)-phthalazinyl,1,2,3,4-tetrahydroquinolinyl, oxindolyl, isoquinolinyl,imidazo[2,1-b][1,3]thiazolyl, 2,3-dihydroimidazo[2,1b][1,3]thiazolyl,1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,4-triazinyl, 1,3,5-triazinyl, indazolyl,3-indazolinone, dihydrobenzofuranyl, phthalide, phthalimide, coumarin,chromone, 1,2,3,4-tetrahydroisoquindine, 1,8-naphthyridinyl,1,7-naphthyridinyl, 1,6-naphthyridinyl, 1,5-naphthyridinyl,1,7-tetrahydronaphthyridinyl, 1,6-tetrahydronaphthyridinyl,isoindolinyl, 4,5-diazaindanyl, 1,4-diazaindanyl, 1,5-diazaindanyl,1,6-diazaindanyl, 1,7-diazaindanyl, triazanaphthalinyl, pteridinyl,purinyl,

[0216] In another embodiment of the present invention, R² is C₁₋₈ alkyl,unsubstituted or substituted with one to three substituentsindependently selected from:

[0217] (a) halogen,

[0218] (b) aryl,

[0219] (c) C₁₋₈ alkyl,

[0220] (d) C₃₋₈ cycloalkyl,

[0221] (e) C₃₋₈ cycloheteroalkyl,

[0222] (f) amino,

[0223] (g) C₁₋₆ alkylamino,

[0224] (h) (C₁₋₆ alkyl)₂amino,

[0225] (i) aryl C₀₋₆ alkylamino,

[0226] (j) (aryl C₀₋₆ alkyl)₂amino,

[0227] (k) C₁₋₆ alkylthio,

[0228] (l) aryl C₀₋₆alkylthio,

[0229] (m) C₁₋₆ alkylsulfinyl,

[0230] (n) aryl C₀₋₆alkylsulfinyl,

[0231] (o) C₁₋₆ alkylsulfonyl,

[0232] (p) aryl C₀₋₆alkylsulfonyl,

[0233] (q) C₁₋₆ alkoxy,

[0234] (r) aryl C₀₋₆ alkoxy,

[0235] (s) hydroxycarbonyl,

[0236] (t) C₁₋₆ alkoxycarbonyl,

[0237] (u) aryl C₀₋₆ alkoxycarbonyl,

[0238] (v) hydroxycarbonyl C₁₋₆ alkyloxy,

[0239] (w) hydroxy,

[0240] (x) cyano,

[0241] (y) nitro,

[0242] (z) perfluoroC₁₋₄alkyl,

[0243] (aa) perfluoroC₁₋₄alkoxy,

[0244] (bb) oxo,

[0245] (cc) C₁₋₆ alkylcarbonyloxy,

[0246] (dd) aryl C₀₋₆alkylcarbonyloxy,

[0247] (ee) C₁₋₆ alkylcarbonylamino,

[0248] (ff) aryl C₀₋₆ alkylcarbonylamino,

[0249] (gg) C₁₋₆ alkylsulfonylamino,

[0250] (hh) aryl C₀₋₆alkylsulfonylamino,

[0251] (ii) C₁₋₆ alkoxycarbonylamino,

[0252] (jj) aryl C₀₆ alkoxycarbonylamino,

[0253] (kk) C₁₋₆alkylaminocarbonylamino,

[0254] (ll) aryl C₀₋₆alkylaminocarbonylamino,

[0255] (mm) (C₁₋₆alkyl)₂ aminocarbonylamino,

[0256] (nn) (aryl C₀₋₆alkyl)₂ aminocarbonylamino,

[0257] (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy,

[0258] (pp) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, and

[0259] (qq) spiro-C₃₋₈cycloalkyl;

[0260] In a class of this embodiment of the present invention, R² isC₁₋₈ alkyl, unsubstituted or substituted with one to three substituentsindependently selected from:

[0261] (a) fluoro,

[0262] (b) chloro,

[0263] (c) aryl,

[0264] (d) C₃₋₆ cycloalkyl,

[0265] (e) C₃₋₆ cycloheteroalkyl,

[0266] (f) amino,

[0267] (g) C₁₋₆ alkylamino,

[0268] (h) (C₁₋₆ alkyl)₂amino,

[0269] (i) aryl C₀₋₆ alkylamino,

[0270] (j) (aryl C₀₋₆ alkyl)₂amino,

[0271] (k) C₁₋₆ alkylthio,

[0272] (l) aryl C₀₋₁alkylthio,

[0273] (m) C₁₋₆ alkylsulfinyl,

[0274] (n) aryl C₀₋₁alkylsulfinyl,

[0275] (o) C₁₋₆ alkylsulfonyl,

[0276] (p) aryl C₀₋₁alkylsulfonyl,

[0277] (q) C₁₋₆ alkoxy,

[0278] (r) aryl C₀₋₁ alkoxy,

[0279] (s) hydroxycarbonyl,

[0280] (t) C₁₋₆ alkoxycarbonyl,

[0281] (u) aryl C₀₋₁ alkoxycarbonyl,

[0282] (v) hydroxycarbonyl C₁₋₆ alkyloxy,

[0283] (w) hydroxy,

[0284] (x) cyano,

[0285] (y) nitro,

[0286] (z) perfluoroC₁₋₄alkyl,

[0287] (aa) trifluoromethoxy,

[0288] (bb) oxo,

[0289] (cc) C₁₋₆ alkylcarbonyloxy,

[0290] (dd) aryl C₀₋₁alkylcarbonyloxy,

[0291] (ee) C₁₋₆ alkylcarbonylamino,

[0292] (ff) aryl C₀₋₁ alkylcarbonylamino,

[0293] (gg) C₁₋₆ alkylsulfonylamino,

[0294] (hh) aryl C₀₋₁alkylsulfonylamino,

[0295] (ii) C₁₋₆ alkoxycarbonylamino,

[0296] (jj) aryl C₀₋₁alkoxycarbonylamino,

[0297] (kk) C₁₋₆alkylaminocarbonylamino,

[0298] (ll) aryl C₀₋₁alkylaminocarbonylamino,

[0299] (mm) (C₁₋₆alkyl)₂ aminocarbonylamino,

[0300] (nn) (aryl C₀₋₁alkyl)₂ aminocarbonylamino,

[0301] (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy,

[0302] (pp) (aryl C₀₋₁alkyl)₂ aminocarbonyloxy, and

[0303] (qq) spiro-cyclopropyl.

[0304] In a subclass of this class of the present invention, R² is C₁₋₈alkyl, unsubstituted or substituted with one to three substituentsindependently selected from:

[0305] (a) fluoro,

[0306] (b) aryl,

[0307] (c) C₅₋₆ cycloheteroalkyl,

[0308] (d) amino,

[0309] (e) C₁₋₆ alkylamino,

[0310] (f) (C₁₋₆ alkyl)₂amino,

[0311] (g) C₁₋₄ alkoxy,

[0312] (h) hydroxy,

[0313] (i) trifluoromethoxy, and

[0314] (j) oxo.

[0315] In another subclass of this embodiment of the present invention,R² is C₁₋₈ alkyl, unsubstituted or substituted with one or twosubstituents independently selected from:

[0316] (a) fluoro,

[0317] (b) chloro,

[0318] (c) phenyl,

[0319] (d) thienyl,

[0320] (e) pyrazinyl,

[0321] (f) C₃₋₆ cycloalkyl,

[0322] (g) C₅₋₆ cycloheteroalkyl,

[0323] (h) amino,

[0324] (i) C₁₋₄ alkylamino,

[0325] (j) (C₁₋₄ alkyl)₂amino,

[0326] (k) benzylamino,

[0327] (l) phenylamino,

[0328] (m) (aryl C₀₋₁ alkyl)₂amino,

[0329] (n) methylthio,

[0330] (o) methoxy,

[0331] (p) hydroxycarbonyl,

[0332] (q) C₁₋₆ alkoxycarbonyl,

[0333] (r) phenyl C₀₋₁ alkoxycarbonyl,

[0334] (s) hydroxy,

[0335] (t) trifluoromethyl,

[0336] (u) trifluoromethoxy,

[0337] (v) oxo, and

[0338] (w) methylcarbonyloxy.

[0339] In one embodiment of the present invention, R² is selected from:methyl, isopropyl, ethyl, and butyl, either unsubstituted orsubstituted.

[0340] In yet another embodiment of the present invention, R² isperfluoroC₁₋₈alkyl. In one class of this embodiment of the presentinvention R² is perfluoroC₁₋₃ alkyl. In a subclass of this embodimentof,the present invention, R² is trifluoromethyl.

[0341] In still another embodiment of the present invention, R² is C₂₋₈alkenyl, unsubstituted or substituted with one to three substituentsindependently selected from:

[0342] (a) halogen,

[0343] (b) aryl,

[0344] (c) C₁₋₈ alkyl,

[0345] (d) C₃₋₈ cycloalkyl,

[0346] (e) C₃₋₈ cycloheteroalkyl,

[0347] (f) amino,

[0348] (g) C₁₋₆ alkylamino,

[0349] (h) (C₁₋₆ alkyl)₂amino, (i) aryl C₀₋₆ alkylamino,

[0350] (j) (aryl C₀₋₆ alkyl)₂amino,

[0351] (k) C₁₋₆ alkylthio,

[0352] (l) aryl C₀₋₆alkylthio,

[0353] (m) C₁₋₆ alkylsulfinyl,

[0354] (n) aryl C₀₋₆alkylsulfinyl,

[0355] (o) C₁₋₆ alkylsulfonyl,

[0356] (p) aryl C₀₋₆alkylsulfonyl,

[0357] (q) C₁₋₆ alkoxy,

[0358] (r) aryl C₀₋₆ alkoxy,

[0359] (s) hydroxycarbonyl,

[0360] (t) C₁₋₆ alkoxycarbonyl,

[0361] (u) aryl C₀₋₆ alkoxycarbonyl,

[0362] (v) hydroxycarbonyl C₁₋₆ alkyloxy,

[0363] (w) hydroxy,

[0364] (x) cyano,

[0365] (y) nitro,

[0366] (z) perfluoroC₁₋₄alkyl,

[0367] (aa) perfluoroC₁₋₄alkoxy,

[0368] (bb) oxo,

[0369] (cc) C₁₋₆ alkylcarbonyloxy,

[0370] (dd) aryl C₀₋₆alkylcarbonyloxy,

[0371] (ee) C₁₋₆ alkylcarbonylamino,

[0372] (ff) aryl C₀₋₆ alkylcarbonylamino,

[0373] (gg) C₁₋₆ alkylsulfonylamino,

[0374] (hh) aryl C₀₋₆alkylsulfonylamino,

[0375] (ii) C₁₋₆ alkoxycarbonylamino,

[0376] (jj) aryl C₀₋₆ alkoxycarbonylamino,

[0377] (kk) C₁₋₆alkylaminocarbonylamino,

[0378] (ll) aryl C₀₋₆alkylaminocarbonylamino,

[0379] (mm) (C₁₋₆alkyl)₂ aminocarbonylamino,

[0380] (nn) (aryl C₀₋₆alkyl)₂ aminocarbonylamino,

[0381] (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy,

[0382] (pp) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, and

[0383] (qq) spiro-C₃₋₈cycloalkyl;

[0384] In one class of this embodiment of the present invention, R² isC₂₋₈ alkenyl, unsubstituted or substituted with one to two substituentsindependently selected from:

[0385] (a) fluoro,

[0386] (b) chloro,

[0387] (c) aryl,

[0388] (d) C₃₋₆ cycloalkyl,

[0389] (e) C₅₋₆ cycloheteroalkyl,

[0390] (f) amino,

[0391] (g) C₁₋₆ alkylamino,

[0392] (h) (C₁₋₆ alkyl)₂amino,

[0393] (i) aryl C₀₋₆ alkylamino,

[0394] (j) (aryl C₀₋₆ alkyl)₂amino,

[0395] (k) C₁₋₆ alkylthio,

[0396] (l) aryl C₀₋₁alkylthio,

[0397] (m) C₁₋₆ alkylsulfinyl,

[0398] (n) aryl C₀₋₁alkylsulfinyl,

[0399] (o) C₁₋₆ alkylsulfonyl,

[0400] (p) aryl C₀₋₁alkylsulfonyl,

[0401] (q) C₁₋₆ alkoxy,

[0402] (r) aryl C₀₋₁ alkoxy,

[0403] (s) hydroxycarbonyl,

[0404] (t) C₁₋₆ alkoxycarbonyl,

[0405] (u) aryl C₀₋₁ alkoxycarbonyl,

[0406] (v) hydroxycarbonyl C₁₋₆ alkyloxy,

[0407] (w) hydroxy,

[0408] (x) cyano,

[0409] (y) nitro,

[0410] (z) perfluoroC₁₋₄alkyl,

[0411] (aa) trifluoromethoxy,

[0412] (bb) oxo,

[0413] (cc) C₁₋₆ alkylcarbonyloxy,

[0414] (dd) aryl C₀₋₁alkylcarbonyloxy,

[0415] (ee) C₁₋₆ alkylcarbonylamino,

[0416] (ff) aryl C₀₋₁ alkylcarbonylamino,

[0417] (gg) C₁₋₆ alkylsulfonylamino,

[0418] (hh) aryl C₀₋₁alkylsulfonylamino,

[0419] (ii) C₁₋₆ alkoxycarbonylamino,

[0420] (jj) aryl C₀₋₁ alkoxycarbonylamino,

[0421] (kk) C₁₋₆alkylaminocarbonylamino,

[0422] (ll) aryl C₀₋₁alkylaminocarbonylamino,

[0423] (mm) (C₁₋₆alkyl)₂ aminocarbonylamino,

[0424] (nn) (aryl C₀₋₁alkyl)₂ aminocarbonylamino,

[0425] (oo) (C₁₋₄alkyl)₂ aminocarbonyloxy, and

[0426] (pp) (aryl C_(0-1 alkyl)) ₂ aminocarbonyloxy.

[0427] In one subclass of this class of this embodiment of the presentinvention, R² is C₂₋₈ alkenyl, unsubstituted or substituted with one totwo substituents independently selected from:

[0428] (a) fluoro,

[0429] (b) chloro,

[0430] (c) phenyl,

[0431] (d) cyclohexyl,

[0432] (e) cyclopropyl,

[0433] (f) C₅₋₆ cycloheteroalkyl,

[0434] (g) amino,

[0435] (h) methylamino,

[0436] (i) dimethylamino,

[0437] (j) benzylamino,

[0438] (k) phenylamino,

[0439] (l) methylthio,

[0440] (m) methoxy,

[0441] (n) hydroxycarbonyl,

[0442] (o) methoxycarbonyl,

[0443] (p) hydroxy,

[0444] (q) trifluoromethyl,

[0445] (r) trifluoromethoxy,

[0446] (s) oxo, and

[0447] (t) methylcarbonyloxy.

[0448] In yet still another embodiment of the present invention, R² isC₃₋₈ cycloalkyl, either unsubstituted or substituted with one to threesubstituents selected from:

[0449] (a) halogen,

[0450] (b) aryl,

[0451] (c) C₁₋₈ alkyl,

[0452] (d) C₃₋₈ cycloalkyl,

[0453] (e) C₃₋₈ cycloheteroalkyl,

[0454] (f) aryl C₁₋₆alkyl,

[0455] (g) amino C₀₋₆alkyl,

[0456] (h) C₁₋₆ alkylamino C₀₋₆alkyl,

[0457] (i) (C₁₋₆ alkyl)₂amino C₀₋₆alkyl,

[0458] (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl,

[0459] (k) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl,

[0460] (l) C₁₋₆ alkylthio,

[0461] (m) aryl C₀₋₆alkylthio,

[0462] (n) C₁₋₆ alkylsulfinyl,

[0463] (o) aryl C₀₋₆alkylsulfinyl,

[0464] (p) C₁₋₆ alkylsulfonyl,

[0465] (q) aryl C₀₋₆alkylsulfonyl,

[0466] (r) C₁₋₆ alkoxy C₀₋₆alkyl,

[0467] (s) aryl C₀₋₆ alkoxy C₁₋₆alkyl,

[0468] (t) hydroxycarbonyl C₀₋₆alkyl,

[0469] (u) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl,

[0470] (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl,

[0471] (w) hydroxycarbonyl C₁₋₆ alkyloxy,

[0472] (x) hydroxy C₀₋₆alkyl,

[0473] (y) cyano,

[0474] (z) nitro,

[0475] (aa) perfluoroC₁₋₄alkyl,

[0476] (bb) perfluoroC₁₋₄alkoxy,

[0477] (cc) oxo,

[0478] (dd) C₁₋₆ alkylcarbonyloxy,

[0479] (ee) aryl C₀₋₆alkylcarbonyloxy,

[0480] (ff) C₁₋₆ alkylcarbonylamino,

[0481] (gg) aryl C₀₋₆ alkylcarbonylamino,

[0482] (hh) C₁₋₆ alkylsulfonylamino,

[0483] (ii) aryl C₀₋₆alkylsulfonylamino,

[0484] (jj) C₁₋₆ alkoxycarbonylamino,

[0485] (kk) aryl C₀₋₆ alkoxycarbonylamino,

[0486] (ll) C₁₋₆alkylaminocarbonylamino,

[0487] (mm) aryl C₀₋₆alkylaminocarbonylamino,

[0488] (nn) (C₁₋₆alkyl)₂ aminocarbonylamino,

[0489] (oo) (aryl C₀₋₆alkyl)₂ aminocarbonylamino,

[0490] (pp) (C₁₋₆alkyl)₂ aminocarbonyloxy,

[0491] (qq) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy,

[0492] (rr) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and

[0493] (ss) spiro-C₃₋₈cycloalkyl.

[0494] In a class of this embodiment of the present invention, R² isC₃₋₈ cycloalkyl, either unsubstituted or substituted with one to threesubstituents selected from:

[0495] (a) halogen,

[0496] (b) aryl,

[0497] (c) C₁₋₆ alkyl,

[0498] (d) C₃₋₈ cycloheteroalkyl,

[0499] (e) benzyl,

[0500] (f) amino,

[0501] (g) C₁₋₆ alkylamino,

[0502] (h) C₁₋₆ alkylthio,

[0503] (i) C₁₋₆ alkoxy,

[0504] (j) hydroxy,

[0505] (k) cyano,

[0506] (l) nitro,

[0507] (m) perfluoroC₁₋₄alkyl,

[0508] (n) trifluoromethoxy,

[0509] (o) oxo,

[0510] (p) methylcarbonyloxy,

[0511] (q) methylcarbonylamino,

[0512] (r) methylsulfonylamino,

[0513] (s) methoxycarbonylamino,

[0514] (t) methylaminocarbonylamino,

[0515] (u) dimethylaminocarbonylamino,

[0516] (v) dimethylaminocarbonyloxy, and

[0517] (w) spiro C₃₋₈ cycloalkyl.

[0518] In a subclass of this class of the present invention, R² is C₃₋₈cycloalkyl, either unsubstituted or substituted with one to threesubstituents selected from:

[0519] (a) fluoro,

[0520] (b) aryl,

[0521] (c) C₁₋₄ alkyl,

[0522] (d) trifluoromethyl,

[0523] (e) C₁₋₃ alkoxy,

[0524] (f) hydroxy,

[0525] (g) oxo, and

[0526] (h) spiro C₃₋₈ cycloalkyl.

[0527] In another subclass of this class of the present invention, R² isC₃₋₈ cycloalkyl, either unsubstituted or substituted with one to twosubstituents selected from:

[0528] (a) fluoro,

[0529] (b) chloro,

[0530] (c) phenyl,

[0531] (d) C₁₋₄ alkyl,

[0532] (e) cyclopropyl,

[0533] (f) cyclohexyl,

[0534] (g) benzyl,

[0535] (h) amino,

[0536] (i) C₁₋₃ alkylamino,

[0537] (j) C₁₋₃ alkoxy,

[0538] (k) hydroxy,

[0539] (ll) trifluoromethyl,

[0540] (m) trifluoromethoxy,

[0541] (n) oxo,

[0542] (o) methylcarbonyloxy,

[0543] (p) methylcarbonylamino,

[0544] (q) methoxycarbonylamino,

[0545] (r) methylaminocarbonylamino, and

[0546] (s) spiro C₃₋₈ cycloalkyl.

[0547] In one embodiment of the present invention, R² is cyclopropyl,unsubstituted or substituted. In another embodiment of the presentinvention, R² is cyclobutyl, unsubstituted or substituted. In yetanother embodiment of the present invention, R² is cyclopentyl,unsubstituted or substituted. In still another embodiment of the presentinvention, R² is cyclohexyl, unsubstituted or substituted. In yet stillanother embodiment of the present invention, R² is cycloheptyl,unsubstituted or substituted. In another embodiment of the presentinvention, R² is cyclooctyl, unsubstituted or substituted.

[0548] In another embodiment of the present invention, R² iscycloheteroalkyl, unsubstituted or substituted with one to threesubstituents selected from:

[0549] (a) halogen,

[0550] (b) aryl,

[0551] (c) C₁₋₈ alkyl,

[0552] (d) C₃₋₈ cycloalkyl,

[0553] (e) C₃₋₈ cycloheteroalkyl,

[0554] (f) aryl C₁₋₆alkyl,

[0555] (g) amino C₀₋₆alkyl,

[0556] (h) C₁₋₆ alkylamino C₀₋₆alkyl,

[0557] (i) (C₁₋₆ alkyl)₂amino-C₀₋₆alkyl,

[0558] (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl,

[0559] (k) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl,

[0560] (l) C₁₋₆ alkylthio,

[0561] (m) aryl C₀₋₆alkylthio,

[0562] (n) C₁₋₆ alkylsulfinyl,

[0563] (o) aryl C₀₋₆alkylsulfinyl,

[0564] (p) C₁₋₆ alkylsulfonyl,

[0565] (q) aryl C₀₋₆alkylsulfonyl,

[0566] (r) C₁₋₆ alkoxy C₀₋₆alkyl,

[0567] (s) aryl C₀₋₆ alkoxy C₀₋₆alkyl,

[0568] (t) hydroxycarbonyl C₀₋₆alkyl,

[0569] (u) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl,

[0570] (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl,

[0571] (w) hydroxycarbonyl C₁₋₆ alkyloxy,

[0572] (x) hydroxy C₀₋₆alkyl,

[0573] (y) cyano,

[0574] (z) nitro,

[0575] (aa) perfluoroC₁₋₄alkyl,

[0576] (bb) perfluoroC₁₋₄alkoxy,

[0577] (cc) oxo,

[0578] (dd) C₁₋₆ alkylcarbonyloxy,

[0579] (ee) aryl C₀₋₆alkylcarbonyloxy,

[0580] (ff) C₁₋₆ alkylcarbonylamino,

[0581] (gg) aryl C₀₋₆ alkylcarbonylamino,

[0582] (hh) C₁₋₆ alkylsulfonylamino,

[0583] (ii) aryl C₀₋₆alkylsulfonylamino,

[0584] (jj) C₁₋₆ alkoxycarbonylamino,

[0585] (kk) aryl C₀₋₆ alkoxycarbonylamino,

[0586] (ll) C₁₋₆alkylaminocarbonylamino,

[0587] (mm) aryl C₀₋₆alkylaminocarbonylamino,

[0588] (nn) (C₁₋₆alkyl)₂ aminocarbonylamino,

[0589] (oo) (aryl C₀₋₆alkyl)₂ aminocarbonylamino,

[0590] (pp) (C₁ ₆alkyl)₂ aminocarbonyloxy,

[0591] (qq) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy,

[0592] (rr) C₀₋₆ alkylcarbonylC₀₋₆ alkyl, and

[0593] (ss) spiro-C₃₋₈cycloalkyl;

[0594] provided that any heteroatom substituent is bonded to a carbonatom in the cycloheteroalkyl ring.

[0595] In one class of this embodiment of the present invention, R² iscycloheteroalkyl, unsubstituted or substituted with one to twosubstituents selected from:

[0596] (a) fluoro,

[0597] (b) chloro,

[0598] (c) aryl,

[0599] (d) C₁₋₄ alkyl,

[0600] (e) benzyl,

[0601] (f) amino,

[0602] (g) C₁₋₆ alkylamino,

[0603] (h) C₁₋₆ alkylthio,

[0604] (i) C₁₋₆ alkoxy,

[0605] (j) hydroxy,

[0606] (k) cyano,

[0607] (l) nitro,

[0608] (m) perfluoroC₁₋₄alkyl,

[0609] (n) trifluoromethoxy,

[0610] (o) oxo,

[0611] (p) methylcarbonyloxy,

[0612] (q) methylcarbonylamino,

[0613] (r) methylsulfonylamino,

[0614] (s) methoxycarbonylamino,

[0615] (t) methylaminocarbonylamino,

[0616] (u) dimethylaminocarbonylamino,

[0617] (v) dimethylaminocarbonyloxy, and

[0618] (w) spiro C₃₋₈ cycloalkyl.

[0619] In a subclass of this class of the present invention, R² iscycloheteroalkyl, either unsubstituted or substituted with one or twosubstituents selected from:

[0620] (a) fluoro,

[0621] (b) phenyl,

[0622] (c) C₁₋₄ alkyl,

[0623] (d) C₁₋₃ alkoxy,

[0624] (e) hydroxy,

[0625] (f) trifluoromethyl,

[0626] (g) oxo, and

[0627] (h) spiro C₃₋₈ cycloalkyl.

[0628] In another subclass of this class of the present invention, R² iscycloheteroalkyl, either unsubstituted or substituted with one to twosubstituents selected from:

[0629] (a) fluoro,

[0630] (b) chloro,

[0631] (c) phenyl,

[0632] (d) C₁₋₄ alkyl,

[0633] (e) benzyl,

[0634] (f) amino,

[0635] (g) C₁₋₃ alkylamino,

[0636] (h) C₁₋₃ alkoxy,

[0637] (i) hydroxy,

[0638] (j) trifluoromethyl,

[0639] (k) trifluoromethoxy, and

[0640] (l) oxo.

[0641] In one embodiment of the present invention R² is selected frompiperidinyl, pyrrolidinyl, azetidinyl, morpholinyl, piperazinyl, andoctahydroquinolizinyl, either unsubstituted or substituted. In anotherembodiment of the present invention, R² is selected from: piperidinyl,pyrrolidinyl, morpholinyl, and octahydro-2H-quinolizinyl, eitherunsubstituted or substituted.

[0642] R³ is selected from H and C₁₋₈ alkyl, or R² and R³, together withthe nitrogen atom to which they are attached, form a 5- to 7-memberedheterocyclic ring, optionally containing one or two additionalheteroatoms selected from N, S, and O, optionally having one or moredegrees of unsaturation, optionally fused to a 6-membered heteroaromaticor aromatic ring, either unsubstituted or substituted with one to threesubstituents selected from:

[0643] (1) halogen,

[0644] (2) aryl,

[0645] (3) C₁₋₈ alkyl,

[0646] (4) C₃₋₈ cycloalkyl,

[0647] (5) C₃₋₈ cycloheteroalkyl,

[0648] (6) aryl C₁₋₆alkyl,

[0649] (7) amino C₀₋₆alkyl,

[0650] (8) C₁₋₆ alkylamino C₀₋₆alkyl,

[0651] (9) (C₁₋₆ alkyl)₂amino C₀₋₆alkyl,

[0652] (10) aryl C₀₋₆ alkylamino C₀₋₆alkyl,

[0653] (11) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl,

[0654] (12) C₁₋₆ alkylthio,

[0655] (13) aryl C₀₋₆alkylthio,

[0656] (14) C₁₋₆ alkylsulfinyl,

[0657] (15) aryl C₀₋₆alkylsulfinyl,

[0658] (16) C₁₋₆ alkylsulfonyl,

[0659] (17) aryl C₀₋₆alkylsulfonyl,

[0660] (18) C₁₋₆ alkoxy C₀₋₆alkyl,

[0661] (19) aryl C₀₋₆ alkoxy C₀₋₆alkyl,

[0662] (20) hydroxycarbonyl C₀₋₆alkyl,

[0663] (21) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl,

[0664] (22) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl,

[0665] (23) hydroxycarbonyl C₁₋₆ alkyloxy,

[0666] (24) hydroxy C₀₋₆alkyl,

[0667] (25) cyano,

[0668] (26) nitro,

[0669] (27) perfluoroC₁₋₄alkyl,

[0670] (28) perfluoroC₁₋₄alkoxy,

[0671] (29) oxo,

[0672] (30) C₁₋₆ alkylcarbonyloxy,

[0673] (31) aryl C₀₋₆alkylcarbonyloxy,

[0674] (32) C₁₋₆ alkylcarbonylamino,

[0675] (33) aryl C₀₋₆ alkylcarbonylamino,

[0676] (34) C₁₋₆ alkylsulfonylamino,

[0677] (35) aryl C₀₋₆alkylsulfonylamino,

[0678] (36) C₁₋₆ alkoxycarbonylamino,

[0679] (37) aryl C₀₋₆ alkoxycarbonylamino,

[0680] (38) C₁₋₆alkylaminocarbonylamino,

[0681] (39) aryl C₀₋₆alkylaminocarbonylamino,

[0682] (40) (C₁₋₆alkyl)₂ aminocarbonylamino,

[0683] (41) (aryl C₀₋₆alkyl)₂ aminocarbonylamino,

[0684] (42) (C₁₋₆alkyl)₂ aminocarbonyloxy,

[0685] (43) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, and

[0686] (44) spiro-C₃₋₈cycloalkyl

[0687] provided that any heteroatom substituent is bonded to a carbonatom in the heterocyclic ring;

[0688] In one class of this embodiment of the present invention, R³ isselected from H and C₁₋₈ alkyl, or R² and R³, together with the nitrogenatom to which they are attached, form a 5- to 7-membered heterocyclicring, optionally containing one additional heteroatom selected from N,S,- and O, optionally fused to a phenyl ring, optionally having one ormore degrees of unsaturation, either unsubstituted or substituted withone to two substituents selected from:

[0689] (1) halogen,

[0690] (2) phenyl,

[0691] (3) C₁₋₃ alkyl,

[0692] (4) methoxy,

[0693] (5) hydroxy,

[0694] (6) cyano,

[0695] (7) nitro,

[0696] (8) trifluoromethyl,

[0697] (9) trifluoromethoxy, and

[0698] (10) oxo,

[0699] provided that any heteroatom substituent is bonded to a carbonatom in the heterocyclic ring.

[0700] In one class of this embodiment of the present invention, R³ isselected from H and C₁₋₈ alkyl, or R² and R³, together with the nitrogenatom to which they are attached, forma C₅₋₇ heterocyclic ring,optionally fused to a phenyl ring, unsubstituted, or substituted withone to three substituents selected from:

[0701] (1) fluoro,

[0702] (2) chloro,

[0703] (3) phenyl,

[0704] (4) methyl,

[0705] (5) methoxy,

[0706] (6) hydroxy,

[0707] (7) cyano,

[0708] (8) nitro,

[0709] (9) trifluoromethyl,

[0710] (10) trifluoromethoxy,

[0711] (11) oxo,

[0712] provided that any heteroatom substituent is bonded to a carbonatom in the heterocyclic ring.

[0713] In one subclass of this embodiment, R² and R³ together form agroup selected from: indolinyl, tetrahydroisoquinolinyl,tetrahydroquinolinyl, piperidinyl, and pyrrolidinyl.

[0714] In one subclass of this class of the present invention, R³ isselected from H and C₁₋₃ alkyl. In a further subclass of the presentinvention, R³ is selected from H and methyl. In still a further subclassof the present invention, R³ is hydrogen.

[0715] In one embodiment of the present invention, R⁴ and R⁵ are eachindependently selected from

[0716] (1) hydrogen,

[0717] (2) halogen,

[0718] (3) phenyl,

[0719] (4) C₁₋₆ alkyl,

[0720] (5) cyclopropyl

[0721] (6) cyclohexyl,

[0722] (7) C₅₋₇ cycloheteroalkyl,

[0723] (8) benzyl,

[0724] (9) amino,

[0725] (10) C₁₋₆ alkylamino,

[0726] (11) (C₁₋₆ alkyl)₂amino,

[0727] (12) aryl amino,

[0728] (13) (aryl)₂amino,

[0729] (14) C₁₋₆ alkylthio,

[0730] (15) arylthio,

[0731] (16) C₁₋₆ alkoxy,

[0732] (17) aryl oxy,

[0733] (18) hydroxycarbonyl,

[0734] (19) C₁₋₆ alkoxycarbonyl,

[0735] (20) aryl C₁₋₆ alkoxycarbonyl,

[0736] (21) hydroxycarbonyl C₁₋₆ alkyloxy,

[0737] (22) hydroxy,

[0738] (23) cyano,

[0739] (24) nitro,

[0740] (25) trifluoromethoxy,

[0741] (26) trifluoromethyl,

[0742] (27) C₁₋₆ alkylcarbonyloxy,

[0743] (28) aryl C₀₋₆alkylcarbonyloxy,

[0744] (29) alkyl C₁₋₆ carbonylamino,

[0745] (30) aryl C₀₋₆ alkylcarbonylamino,

[0746] (31) C₁₋₆ alkoxycarbonylamino,

[0747] (32) aryl C₀₋₆ alkoxycarbonylamino,

[0748] (33) C₁₋₆alkylaminocarbonylamino,

[0749] (34) aryl C₀₋₆alkylaminocarbonylamino,

[0750] (35) (C₁₋₆alkyl)₂ aminocarbonylamino,

[0751] (36) (aryl C₀₋₆alkyl)₂ aminocarbonylamino,

[0752] (37) (C₁₋₆alkyl)₂ aminocarbonyloxy,

[0753] (38) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and

[0754] (39) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy,

[0755] or, R⁴ and R⁵ together form an oxo group or ═CH—R⁶ or aspiro-C₃₋₇ cycloalkyl ring, unsubstituted or substituted with R⁶;

[0756] In another embodiment of the present invention, R⁴ and R⁵ areeach independently selected from:

[0757] (1) hydrogen,

[0758] (2) fluoro,

[0759] (3) chloro,

[0760] (4) phenyl,

[0761] (5) C₁₋₃ alkyl,

[0762] (6) cyclopropyl

[0763] (7) benzyl,

[0764] (8) amino,

[0765] (9) C₁₋₃ alkoxy,

[0766] (10) phenyloxy,

[0767] (11) hydroxycarbonyl,

[0768] (12) hydroxy,

[0769] (13) cyano,

[0770] (14) nitro,

[0771] (15) trifluoromethoxy, and

[0772] (16) trifluoromethyl,

[0773] or, R⁴ and R⁵ together form an oxo group or ═CH—R⁶ or aspiro-cyclopropyl ring, unsubstituted or substituted with R⁶.

[0774] In a class of this embodiment of the present invention, R⁴ and R⁵are each independently selected from

[0775] (1) hydrogen,

[0776] (2) fluoro,

[0777] (3) chloro,

[0778] (4) methyl,

[0779] (5) ethyl,

[0780] (6) methoxy,

[0781] (7) hydroxy,

[0782] (8) trifluoromethoxy, and

[0783] (9) trifluoromethyl,

[0784] or, R⁴ and R⁵ together form an oxo group.

[0785] In a subclass of this class, R⁴ and R⁵ are each hydrogen.

[0786] In one embodiment of the present invention R⁶ is selected fromhydrogen and methyl. In one class of this subclass, R⁶ is hydrogen.

[0787] Particular compounds of structural formula (I) include:

[0788] N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0789]N-(2-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0790]N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0791]N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0792]N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0793]N-(2-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0794]N-(4-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0795]N-(3-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0796]N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0797]N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0798]N-(3-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0799]N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0800]N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0801]N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0802]N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0803]N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0804]N-(2-methyl-4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0805]N-(4-methoxy-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0806]N-(4-chloro-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0807]N-(2,4-dimethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0808]N-(3-bromo-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0809]N-(2,2,2-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0810]N-(2-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0811] N-(butyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0812]N-(5-methyl-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0813]N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0814]N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0815]N-(4-bromo-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0816]N-(4-chloro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0817]N-(2,4-dichlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0818]N-(3-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0819]N-(4-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0820]N-(5-fluoro-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0821]N-(5-chloro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0822] N-(benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0823]N-((S)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0824]N-((R)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0825]N-(2-phenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0826]N-(1-(3-phenylpropyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0827]N-(3-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0828]N-(2-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0829]N-(2-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0830]N-(3-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0831]N-(3-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0832]N-(4-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0833]N-(3-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0834]N-(2-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0835]N-(cyclohexylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0836]N-(3-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0837]N-(2-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0838]N-(3-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0839]N-(4-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0840]N-(3-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0841]N-(3-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0842]N-(4-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0843]N-(2-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0844]N-(4-methoxylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0845]N-(4-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0846]N-((R)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0847]N-((S)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0848]N-(3-(1-pyrrolidin-2-one)-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0849]N-(2-furanylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0850]N-(1-naphthylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0851]N-(2-(4-imidazoylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0852]N-(2-(3-indolylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0853]N-(5-indolyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0854]N-((1,2-methylenedioxy)-4-benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0855]N-(1,2-diphenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0856]N-(2-(1-hydroxy-1-phenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0857]N-(2-(2-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0858]N-(3-(1-imidazolyl)-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0859]N-(2-(2-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0860]N-(2-methoxyethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0861]N-(4-fluoro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0862]N-(2,4-difluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0863]N-(4-fluoro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0864]N-(4-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0865]N-(2-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0866]N-(3-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0867]N-(3,4-difluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0868]N-(4-dimethylaminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0869]N-(2-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0870]N-(2-benzamidazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0871]N-(1-(4-phenylbutyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0872]N-(3,5-dimethoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0873]N-(2-(2-pyridinylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0874]N-(2-methyl-5-pyrazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0875]N-(2-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0876]N-(2-(2-thiophenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0877]N-(1-(1-naphthyl)-1(R)-ethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0878]N-(2-(3-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0879]N-(2-(2-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0880]N-(2-(4-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0881]N-(4-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0882]N-(2-(3-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0883]N-(2-(3,4-methylenedioxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0884]N-(2-thiophenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0885]N-(2-(4-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0886]N-(2-aminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0887]N-(2-(4-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0888] N-((1S, 2R)2-hydroxy-1-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0889]N-(2-dimethylaminoethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0890] N-(phenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0891]N-(2-chlorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0892]N-(2-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0893]N-(2-trifluoromethoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0894]N-(2-methoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0895] N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0896]N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0897]N-(1,1,1-trifluoroethyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0898]N-(2-propyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0899]N-(2-biphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0900]N-(2-acetylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0901]N-(3-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0902]N-(2-pyridinyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0903]N-(3-pyridinyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0904]N-(2-methylsulfonylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0905]N-(2-methylsulfoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0906] N-(phenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0907]N-(2-chlorophenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0908]N-(2-trifluoromethylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0909]N-(3-methylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0910]N-(2-methylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0911]N-(2-cyanophenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0912]N-(2-benzoylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0913]N-(1,1,1-trifluoroethyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0914] N-(phenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0915]N-(2-chlorophenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0916]N-(2-trifluoromethylphenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0917] N-(phenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0918]N-(2-trifluoromethylphenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0919]N-(2-chlorophenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,

[0920]N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,

[0921]N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,

[0922]N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,

[0923]N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,

[0924]N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,

[0925]N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,

[0926] N-(phenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide

[0927]N-(2-methoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,

[0928] N-(2-propyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,

[0929] N-(2-biphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,

[0930] N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,

[0931]N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,

[0932]N-(1,1,1-trifluoroethyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,

[0933]N-(4-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,

[0934]N-(1,1,1-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0935] N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamid,

[0936]N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0937]N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0938]N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0939]N-(2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0940]N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0941]N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0942]N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0943]N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0944]N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0945]N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0946]N-(3-methoxyphenyl)-3-oxo-4-methyl-4-ata-5α-androst-5-ene-17β-carboxamide,

[0947]N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0948]N-(phenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0949]N-(2-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0950]N-(2-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0951]N-(3-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0952]N-(3-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0953]N-(4-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0954]N-(2-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0955]N-(4-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0956]N-(3-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0957]N-(4-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0958]N-(2-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0959]N-(3-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,

[0960]N-(4-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,and

[0961]N-(1,1,1-trifluoroethyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,and pharmaceutically acceptable salts thereof.

[0962] The term “alkyl” shall mean straight or branched chain alkanes ofone to ten total carbon atoms, or any number within this range (i.e.,methyl, ethyl, 1-propyl, 2-propyl, n-butyl, s-butyl, t-butyl, etc.). Theterm “C₀ alkyl” (as in “C₀₋₈ alkylaryl”) shall refer to the absence ofan alkyl group.

[0963] The term “alkenyl” shall mean straight or branched chain alkenesof two to ten total carbon atoms, or any number within this range.

[0964] The term “alkynyl” shall mean straight or branched chain alkynesof two to ten total carbon atoms, or any number within this range.

[0965] The term “cycloalkyl” shall mean cyclic rings of alkanes of threeto eight total carbon atoms, or any number within this range (i.e.,cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl orcyclooctyl).

[0966] The term “cycloheteroalkyl;” as used herein, shall mean a 3- to8-membered fully saturated heterocyclic ring containing one or twoheteroatoms chosen from N, O, or S and optionally fused to another fullysaturated ring. Examples of cycloheteroalkyl groups include, but are notlimited to piperidinyl, pyrrolidinyl, azetidinyl, morpholinyl,piperazinyl, and octahydroquinolizinyl. In one embodiment of the presentinvention cycloheteroalkyl is selected from piperidinyl, pyrrolidinyl,and morpholinyl.

[0967] The term “alkoxy,” as used herein, refers to straight or branchedchain alkoxides of the number of carbon atoms specified (e.g., C₁₋₅alkoxy), or any number within this range (i.e., methoxy, ethoxy, etc.).

[0968] The term “aryl,” as used herein, refers to a monocyclic orbicyclic system comprising at least one aromatic ring, wherein themonocylic or bicyclic system contains 0, 1, 2, 3, or 4 heteroatomschosen from N, O, or S, and wherein the monocylic or bicylic system iseither unsubstituted or substituted with one or more groupsindependently selected from hydrogen, halogen, aryl, C₁₋₈ alkyl, C₃₋₈cycloalkyl, C₃₋₈ cycloheteroalkyl, aryl C₁₋₆alkyl, amino C₀₋₆alkyl, C₁₋₆alkylamino C₀₋₆alkyl, (C₁₋₆ alkyl)₂amino C₀₋₆alkyl, aryl C₀₋₆ alkylaminoC₀₋₆alkyl, (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, C₁₋₆ alkylthio, arylC₀₋₆alkylthio, C₁₋₆ alkylsulfinyl, aryl C₀₋₆alkylsulfinyl, C₁₋₆alkylsulfonyl, aryl C₀₋₆alkylsulfonyl, C₁₋₆ alkoxy C₀₋₆alkyl, aryl C₀₋₆alkoxy C₀₋₆alkyl, hydroxycarbonyl C₀₋₆alkyl, C₁₋₆ alkoxycarbonylC₀₋₆alkyl, aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, hydroxycarbonyl C₁₋₆alkyloxy, hydroxy C₀₋₆alkyl, cyano, nitro, perfluoroC₁₋₄alkyl,perfluoroC₁₋₄alkoxy, oxo, C₁₋₆ alkylcarbonyloxy, arylC₀₋₆alkylcarbonyloxy, C₁₋₆ alkylcarbonylamino, aryl C₀₋₆alkylcarbonylamino, C₁₋₆ alkylsulfonylamino, arylC₀₋₆alkylsulfonylamino, C₁₋₆ alkoxycarbonylamino, aryl C₀₋₆alkoxycarbonylamino, C₁₋₆alkylaminocarbonylamino, arylC₀₋₆alkylaminocarbonylamino, (C₁₋₆alkyl)₂ aminocarbonylamino, (arylC₀₋₆alkyl)₂ aminocarbonylamino, (C₁₋₆alkyl)₂ aminocarbonyloxy, (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and C₀₋₆alkylcarbonyl C₀₋₆ alkyl. Examplesof aryl include, but are not limited to, phenyl, naphthyl, pyridyl,pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, imidazolyl, benzimidazolyl,benzthiazolyl, benzoxazolyl, indolyl, thienyl, furyl, dihydrobenzofuryl,benzo(1,3)dioxolanyl, benzo(1,4)dioxanyl, oxazolyl, isoxazolyl,thiazolyl, quinolinyl, isothiazolyl, indanyl, isoquinolinyl,dihydroisoquinolinyl, tetrahydronaphthyridinyl, benzothienyl,imidazopyridinyl, tetrahydrobenzazepinyl, quinoxalinyl,imidazopyrimidinyl, cyclopentenopyridinyl, phthalazinyl,tetrahydroquinolinyl, oxindolyl, isoquinolinyl, imidazothiazolyl,dihydroimidazothiazolyl;. tetrazolyl, triazolyl, pyridazinyl,piperidinyl, piperazinyl, oxadiazolyl, thiadiazolyl, triazinyl,indazolyl, indazolinone, dihydrobenzofuranyl, phthalide, phthalimide,coumarin, chromone, tetrahydroisoquindine, naphthyridinyl,tetrahydronaphthyridinyl, isoindolinyl, triazanaphthalinyl, pteridinyl,and purinyl, which are either unsubstituted or substituted with one ormore groups independently selected from hydrogen, halogen, aryl, C₁₋₈alkyl, C₃₋₈ cycloalkyl, C₃₋₈ cycloheteroalkyl, aryl C₁₋₆alkyl, aminoC₀₋₆alkyl, C₁₋₆ alkylamino C₀₋₆alkyl, (C₁₋₆ alkyl)₂amino C₀₋₆alkyl, arylC₀₋₆ alkylamino C₀₋₆alkyl, (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, C₁₋₆alkylthio, aryl C₀₋₆alkylthio, C₁₋₆ alkylsulfinyl, arylC₀₋₆alkylsulfinyl, C₁₋₆ alkylsulfonyl, aryl C₀₋₆alkylsulfonyl, C₁₋₆alkoxy C₀₋₆alkyl, aryl C₀₋₆ alkoxy C₀₋₆alkyl, hydroxycarbonyl C₀₋₆alkyl,C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl,hydroxycarbonyl C₁₋₆ alkyloxy, hydroxy C₀₋₆alkyl, cyano, nitro,perfluoroC₁₋₄alkyl, perfluoroC₁₋₄alkoxy, oxo, C₁₋₆ alkylcarbonyloxy,aryl C₀₋₆alkylcarbonyloxy, C₁₋₆ alkylcarbonylamino, aryl C₀₋₆alkylcarbonylamino, C₁₋₆ alkylsulfonylamino, arylC₀₋₆alkylsulfonylamino, C₁₋₆ alkoxycarbonylamino, aryl C₀₋₆alkoxycarbonylamino, C₁₋₆alkylaminocarbonylamino, arylC₀₋₆alkylaminocarbonylamino, (C₁₋₆alkyl)₂ aminocarbonylamino, (arylC₀₋₆alkyl)₂ aminocarbonylamino, (C₁₋₆alkyl)₂ aminocarbonyloxy, (arylC₀₋₆alkyl)₂ aminocarbonyloxy, C₀₋₆alkylcarbonyl C₀₋₆alkyl andarylC₀₋₆alkylcarbonyl C₀₋₆alkyl. In one embodiment of the presentinvention, aryl is selected from phenyl, pyridyl, pyrazolyl,benzamidazolyl, imidazolyl, furyl, napthyl, indolyl, indanyl, thienyl,pyrazinyl, benzothienyl, 3,4-dihydro-1(1H)-isoquinolinyl,1-8-tetrahydronaphthyridinyl, imidazo[1,2-a]pyridinyl,2-oxo-2,3,4,5-tetrahydro-1H-benzo[B]azepinyl, quinoxalinyl,imidazo[1,2-a]pyrimidinyl, 2-3-cyclopentenopyridinyl,1-(2H)-phthalazinyl, 1,2,3,4-tetrahydroquinolinyl, oxindolyl,isoquinolinyl, imidazo[2,1-b][1,3]thiazolyl,2,3-dihydroimidazo[2,1-b][1,3]thiazolyl, and quinolinyl. Preferably, thearyl group is unsubstituted, mono-, di-, or tri- substituted with one tothree of the above-named substituents; more preferably, the aryl groupis unsubstituted, mono- or di-substituted with one to two of theabove-named substituents.

[0969] Whenever the term “alkyl” or “aryl” or either of their prefixroots appears in a name of a substituent (e.g., aryl C₀₋₈ alkyl), itshall be interpreted as including those limitations given above for“alkyl” and “aryl.” Designated numbers of carbon atoms (e.g., C₀₋₈)shall refer independently to the number of carbon atoms in an alkyl orcyclic alkyl moiety or to the alkyl portion of a larger substituent inwhich alkyl appears as its prefix root.

[0970] The terms “arylalkyl” and “alkylaryl” include an alkyl portionwhere alkyl is as defined above and to include an aryl portion wherearyl is as defined above. Examples of arylalkyl include, but are notlimited to, benzyl, fluorobenzyl, chlorobenzyl, phenylethyl,phenylpropyl, fluorophenylethyl, chlorophenylethyl, thienylmethyl,thienylethyl, and thienylpropyl. Examples of alkylaryl include, but arenot limited to, toluene, ethylbenzene, propylbenzene, methylpyridine,ethylpyridine, propylpyridine and butylpyridine.

[0971] The term “halogen” shall include iodine, bromine, chlorine, andfluorine.

[0972] The term “oxy” means an oxygen (O) atom. The term “thio” means asulfur (S) atom. The term “oxo” means “═O”. The term “carbonyl” means“C═O.”

[0973] When any variable (e.g., R³, R⁴, etc.) occurs more than one timein any constituent or in formula I, its definition on each occurrence isindependent of its definition at every other occurrence. Also,combinations of substituents and/or variables are permissible only ifsuch combinations result in stable compounds.

[0974] Under standard nonmenclature used throughout this disclosure, theterminal portion of the designated side chain is described first,followed by the adjacent functionality toward the point of attachment.For example, a C₁₋₅ alkylcarbonylamino C₁₋₆ alkyl substituent isequivalent to

[0975] In choosing compounds of the present invention, one of ordinaryskill in the art will recognize that the various substituents, i.e. R¹,R², R³, etc., are to be chosen in conformity with well-known principlesof chemical structure connectivity.

[0976] The term “substituted” shall be deemed to include multipledegrees of substitution by a named substitutent. Where multiplesubstituent moieties are disclosed or claimed, the substituted compoundcan be independently substituted by one or more of the disclosed orclaimed substituent moieties, singly or plurally. By independentlysubstituted, it is meant that the (two or more) substituents can be thesame or different.

[0977] Representative compounds of the present invention typicallydisplay submicromolar affinity for the androgen receptor. Compounds ofthis invention are therefore useful in treating mammals suffering fromdisorders related to androgen receptor function. Pharmacologicallyeffective amounts of the compound, including the pharmaceuticallyeffective salts thereof, are administered to the mammal, to treatdisorders related to androgen receptor function, or which can beimproved by the addition of additional androgen, such as osteoporosis,periodontal disease, bone fracture, bone damage following bonereconstructive surgery, sarcopenia, frailty, aging skin, malehypogonadism, post-menopausal symptoms in women, atherosclerosis,hypercholesterolemia, hyperlipidemia, aplastic anemia and otherhematopoietic disorders, pancreatic cancer, renal cancer, arthritis andjoint repair. In addition, the compounds of the present invention areuseful in treating osteoporosis and/or bone weakening induced byglucocorticoid administration.

[0978] It is generally preferable to administer compounds of the presentinvention as enantiomerically pure formulations. Racemic mixtures can beseparated into their individual enantiomers by any of a number ofconventional methods. These include chiral chromatography,derivatization with a chiral auxillary followed by separation bychromatography or crystallization, and fractional crystallization ofdiastereomeric salts.

[0979] As used herein, a compound that binds to an intracellularreceptor, such as the androgen receptor, and mimics the effect of thenatural ligand is referred to as an “agonist”; whereas, a compound thatinhibits the effect of the natural ligand is called an “antagonist.” Theterm “tissue selective androgen receptor modulator” refers to to anandrogen receptor ligand that mimics the action of the natural ligand insome tissues but not in others.

[0980] Compounds according to the present invention may be preparedaccording to the procedures outlined in Scheme A and as detailed in theExamples.

[0981] Following procedures described by Rasmusson et al (J. Med. Chem.,1986, 29, 2298-2315), the keto-acid II may be reacted with an amine in asolvent such as ethylene glycol at elevated temperature to producecompounds of structure III. When ammonia is used as the amine theproduct is an unsubstituted lactam. In this case (III, R¹R¹═H), thenitrogen may then be alkylated by treatment of the lactam with a basesuch as sodium hydride in an aprotic solvent (e.g. tetrahydrofuran,“THF”) followed by reaction with an appropriate electrophile.4-Azasteroids of structure IV may be obtained by reduction of the5,6-double bond of III using hydrogen gas and a catalyst such aspalladium on carbon in an organic solvent. Such solvents include ethylacetate, ethanol and methanol. Alternatively, the 5,6-double bond may besaturated using a reducing agent such as sodium cyanoborohydride in thepresence of an acid, for example trifluoroacetic acid, in a suitableorganic solvent. A second route to compounds of structure IV involvesthe catalytic reduction of the 1,2-double bond of V.

[0982] The preparation of 4-azasteroids of general structure V involvesthe dehydrogenation of compound IV. Methods to achieve this aredescribed in U.S. Pat. No. 5,302,621. Similarly, the introduction of a1,2-double bond into In will yield the 1,2 and 5,6-unsaturated 4-azasteroids VI. Such methods include dehydrogenation using2,3-dichloro-5,6-dicyano-p-benzoquinone in the presence of a silylatingagent. A second method requires the treatment of IV (or III) withbenzeneseleninic anhydride in an inert solvent at elevated temperature.Alternatively, reaction of IV (or III) with a base such as diisopropyllithium amide followed by treatment with a diaryl sulfide allows theintroduction of a 2-arylthioether. This 2-arylthioether may then beoxidized (e.g. with a peracid) to produce a sulfoxide which is theneliminated to yield V (or VI). 4-Unsubstituted 4-azasteroids (III-VI)can be alkylated on nitrogen to produce 4-substituted 4-azasteroids.This transformation can be accomplished using a base such as sodiumhydride in an aprotic solvent (e.g., THF) followed by reaction with anelectrophile such as an alkylbromide or alkyliodide.

[0983] Formation of the C-17 amide bond to give VIII is readily achievedfrom the corresponding acid VII by activation of the acid and thenreaction with the required amine ( U.S. Pat. No. 5,302,621). Methodsused to activate the acid include treatment with 1,2-dichloroethane“EDC” and 1-hydroxybenzotriazole “HOBT” (or 1-hydroxy-7-azabenzotriazole“HOAT”) in a solvent such as dimethylformamide “DMF”. A second methodinvolves the formation of a thiopyridylester followed by displacementwith an amine which may be aided by the presence of silver salts (e.g.silver triflate). A third method requires the formation of the acidchloride from the acid. A fourth method involves the use ofcarbonyldiimidazole to generate the imidazolide intermediate ( U.S. Pat.No. 5,237,061). Reaction of this with a substituted amino magnesiumregent then generates the desired C-17 amide. Additionally, it ispossible to form a mixed anhydride and then use this to generate theamide by methods readily appreciated by one of ordinary skill in theart.

[0984] The term “pharmaceutically acceptable salt” is intended toinclude all acceptable salts such as acetate, lactobionate,benzenesulfonate, laurate, benzoate, malate, bicarbonate, maleate,bisulfate, mandelate, bitartrate, mesylate, borate, methylbromide,bromide, methylnitrate, calcium edetate, methylsulfate, camsylate,mucate, carbonate, napsylate, chloride, nitrate, clavulanate,N-methylglucamine, citrate, ammonium salt, dihydrochloride, oleate,edetate, oxalate, edisylate, pamoate (embonate), estolate, palmitate,esylate, pantothenate, fumarate, phosphate/diphosphate, gluceptate,polygalacturonate, gluconate, salicylate, glutamate, stearate,glycollylarsanilate, sulfate, hexylresorcinate, subacetate, hydrabamine,succinate, hydrobromide, tannate, hydrochloride, tartrate,hydroxynaphthoate, teoclate, iodide, tosylate, isothionate,triethiodide, lactate, panoate, valerate, and the like which can be usedas a dosage form for modifying the solubility or hydrolysischaracteristics or can be used in sustained release or pro-drugformulations.

[0985] The term “therapeutically effective amount” means the amount thecompound of structural formula I that will elicit the biological ormedical response of a tissue, system, animal or human that is beingsought by the researcher, veterinarian, medical doctor or otherclinician.

[0986] The term “composition” as used herein is intended to encompass aproduct comprising the specified ingredients in the specified amounts,as well as any product which results, directly or indirectly, fromcombination of the specified ingredients in the specified amounts.

[0987] By “pharmaceutically acceptable” it is meant the carrier, diluentor excipient must be compatible with the other ingredients of theformulation and not deleterious to the recipient thereof.

[0988] The terms “administration of” and or “administering a” compoundshould be understood to mean providing a compound of the invention or aprodrug of a compound of the invention to the individual in need oftreatment.

[0989] The administration of the compound of structural formula I inorder to practice the present methods of therapy is carried out byadministering an effective amount of the compound of structural formulaI to the patient in need of such treatment or prophylaxis. The need fora prophylactic administration according to the methods of the presentinvention is determined via the use of well known risk factors. Theeffective amount of an individual compound is determined, in the finalanalysis, by the physician in charge of the case, but depends on factorssuch as the exact disease to be treated, the severity of the disease andother diseases or conditions from which the patient suffers, the chosenroute of administration other drugs and treatments which the patient mayconcomitantly require, and other factors in the physician's judgment.

[0990] Generally, the daily dosage of the compound of structural formulaI may be varied over a wide range from 0.01 to 1000 mg per adult humanper day. Most preferably, dosages range from 0.1 to 200 mg/day. For oraladministration, the compositions are preferably provided in the form oftablets containing 0.01 to 1000 mg, particularly 0.01, 0.05, 0.1, 0.5,1.0, 2.5, 3.0, 5.0, 6.0, 10.0, 15.0, 25.0, 50.0, 75, 100, 125, 150, 175,180, 200, 225, and 500 milligrams of the active ingredient for thesymptomatic adjustment of the dosage to the patient to be treated.

[0991] The dose may be administered in a single daily dose or the totaldaily dosage may be administered in divided doses of two, three or fourtimes daily. Furthermore, based on the properties of the individualcompound selected for administration, the dose may be administered lessfrequently, e.g., weekly, twice weekly, monthly, etc. The unit dosagewill, of course, be correspondingly larger for the less frequentadministration.

[0992] When administered via intranasal routes, transdermal routes, byrectal or vaginal suppositories, or through a continual intravenoussolution, the dosage administration will, of course, be continuousrather than intermittent throughout the dosage regimen.

[0993] Exemplifying the invention is a pharmaceutical compositioncomprising any of the compounds described above and a pharmaceuticallyacceptable carrier. Also exemplifying the invention is a pharmaceuticalcomposition made by combining any of the compounds described above and apharmaceutically acceptable carrier. An illustration of the invention isa process for making a pharmaceutical composition comprising combiningany of the compounds described above and a pharmaceutically acceptablecarrier.

[0994] Formulations of the tissue selective androgen receptor modulatoremployed in the present method for medical use comprise the compound ofstructural formula I together with an acceptable carrier thereof andoptionally other therapeutically active ingredients. The carrier must bepharmaceutically acceptable in the sense of being compatible with theother ingredients of the formulation and not deleterious to therecipient subject of the formulation.

[0995] The present invention, therefore, further provides apharmaceutical formulation comprising the compound of structural formulaI together with a pharmaceutically acceptable carrier thereof.

[0996] The formulations include those suitable for oral, rectal,intravaginal, topical or parenteral (including subcutaneous,intramuscular and intravenous administration). Preferred are thosesuitable for oral administration.

[0997] The formulations may be presented in a unit dosage form and maybe prepared by any of the methods known in the art of pharmacy. Allmethods include the step of bringing the active compound in associationwith a carrier which constitutes one or more ingredients. In general,the formulations are prepared by uniformly and intimately bringing theactive compound in association with a liquid carrier, a waxy solidcarrier or a finely divided solid carrier, and then, if needed, shapingthe product into desired dosage form.

[0998] Formulations of the present invention suitable for oraladministration may be presented as discrete units such as capsules,cachets, tablets or lozenges, each containing a predetermined amount ofthe active compound; as a powder or granules; or a suspension orsolution in an aqueous liquid or non-aqueous liquid, e.g., a syrup, anelixir, or an emulsion.

[0999] A tablet may be made by compression or molding, optionally withone or more accessory ingredients. Compressed tablets may be prepared bycompressing in a suitable machine the active compound in a free flowingform, e.g., a powder or granules, optionally mixed with accessoryingredients, e.g., binders, lubricants, inert diluents, disintegratingagents or coloring agents. Molded tablets may be made by molding in asuitable machine a mixture of the active compound, preferably inpowdered form, with a suitable carrier. Suitable binders include,without limitation, starch, gelatin, natural sugars such as glucose orbeta-lactose, corn sweeteners, natural and synthetic gums such asacacia, tragacanth or sodium alginate, carboxymethyl-cellulose,polyethylene glycol, waxes and the like. Lubricants used in these dosageforms include, without limitation, sodium-oleate, sodium stearate,magnesium stearate, sodium benzoate, sodium acetate, sodium chloride andthe like. Disintegrators include, without limitation, starch, methylcellulose, agar, bentonite, xanthan gum and the like.

[1000] Oral liquid forms, such as syrups or suspensions in suitablyflavored suspending or dispersing agents such as the synthetic andnatural gums, for example, tragacanth, acacia, methyl cellulose and thelike may be made by adding the active compound to the solution orsuspension. Additional dispersing agents which may be employed includeglycerin and the like.

[1001] Formulations for vaginal or rectal administration may bepresented as a suppository with a conventional carrier, i.e., a basethat is nontoxic and nonirritating to mucous membranes, compatible withthe compound of structural formula I, and is stable in storage and doesnot bind or interfere with the release of the compound of structuralformula I. Suitable bases include: cocoa butter (theobroma oil),polyethylene glycols (such as carbowax and polyglycols),glycol-surfactant combinations, polyoxyl 40 stearate, polyoxyethylenesorbitan fatty acid esters (such as Tween, Myrj, and Arlacel),glycerinated gelatin, and hydrogenated vegetable oils. When glycerinatedgelatin suppositories are used, a preservative such as methylparaben orpropylparaben may be employed.

[1002] Topical preparations containing the active drug component can beadmixed with a variety of carrier materials, well known in the art, suchas, e.g., alcohols, aloe vera gel, allantoin, glycerine, vitamin A and Eoils, mineral oil, PPG2 myristyl propionate, and the like, to form,e.g., alcoholic solutions, topical cleansers, cleansing creams, skingels, skin lotions, and shampoos in cream or gel formulations.

[1003] The compounds of the present invention can also be administeredin the form of liposome delivery systems, such as small unilamellarvesicles, large unilamellar vesicles and multilamellar vesicles.Liposomes can be formed from a variety of phospholipids, such ascholesterol, stearylamine or phosphatidylcholines.

[1004] Compounds of the present invention may also be delivered by theuse of monoclonal antibodies as individual carriers to which thecompound molecules are coupled. The compounds of the present inventionmay also be coupled with soluble polymers as targetable drug carriers.Such polymers can include polyvinyl-pyrrolidone, pyran copolymer,polyhydroxypropylmethacrylamide-phenol,polyhydroxy-ethylaspartamidephenol, or polyethylene-oxide polylysinesubstituted with palmitoyl residues. Furthermore, the compounds of thepresent invention may be coupled to a class of biodegradable polymersuseful in achieving controlled release of a drug, for example,polylactic acid, polyepsilon caprolactone, polyhydroxy butyric acid,polyorthoesters, polyacetals, polydihydropyrans, polycyanoacrylates andcross-linked or amphipathic block copolymers of hydrogels.

[1005] Formulations suitable for parenteral administration includeformulations that comprise a sterile aqueous preparation of the activecompound which is preferably isotonic with the blood of the recipient.Such formulations suitably comprise a solution or suspension of acompound that is isotonic with the blood of the recipient subject. Suchformulations may contain distilled water, 5% dextrose in distilled wateror saline and the active compound. Often it is useful to employ apharmaceutically and pharmacologically acceptable acid addition salt ofthe active compound that has appropriate solubility for the solventsemployed. Useful salts include the hydrochloride isothionate andmethanesulfonate salts. Useful formulations also comprise concentratedsolutions or solids comprising the active compound which on dilutionwith an appropriate solvent give a solution suitable for parenteraladministration.

[1006] The compounds of the present invention may be coupled to a classof biodegradable polymers useful in achieving controlled release of adrug, for example, polylactic acid, polyepsilon caprolactone,polyhydroxy butyric acid, polyorthoesters, polyacetals,polydihydropyrans, polycyanoacrylates and cross-linked or amphipathicblock copolymers of hydrogels.

[1007] The pharmaceutical composition and method of the presentinvention may further comprise other therapeutically active compoundsusually applied in the treatment of the above mentioned conditions,including: osteoporosis, periodontal disease, bone fracture, bone damagefollowing bone reconstructive surgery, sarcopenia, frailty, aging skin,male hypogonadism, post-menopausal symptoms in women, atherosclerosis,hypercholesterolemia, hyperlipidemia, aplastic anemia and otherhematopoietic disorders, pancreatic cancer, renal cancer, arthritis andjoint repair.

[1008] For the treatment and prevention of osteoporosis, the compoundsof the present invention may be administered in combination with abone-strengthening agent selected from: resorption inhibitors,osteoanabolic agents, and other agents beneficial for the skeletonthrough the mechanisms which are not precisely defined, such as calciumsupplements, flavenoids and vitamin D analogues. For example, thecompounds of the instant invention may be effectively administered incombination with effective amounts of other agents such as estrogens,bisphosphonates, SERMs, cathepsin K inhibitors, osteoclast integrininhibitors, vacuolar proton pump inhibitors, VEGF, thiazolidinediones,calcitonin, protein kinase inhibitos, parathyroid hormone andderivatives, calcium receptor antagonists, growth hormone secretagogues,growth hormone releasing hormone, insulin-like growth factor, bonemorphogenic protein (BMP), inhibitors of BMP antagonism, prostaglandinderivatives, fibroblast growth factors, vitamin D and derivativesthereof, Vitamin K and derivatives thereof, soy isoflavones, calcium,and fluoride salts. The conditions of periodontal disease, bonefracture, bone damage following bone reconstructive surgery may alsobenefit from these combined treatments.

[1009] In the treatment of osteoporosis, the activity of the compoundsof the present invention are distinct from that of the resorptioninhibitors: estrogens, bisphosphonates, SERMs, calcitonin and cathepsinK inhibitors, vacuolar proton pump inhibitors, agents interfering withthe RANK/RANKL/ Osteoprotegerin pathway, p38 inhibitors or any otherinhibitors of osteoclast generation or osteoclast activation Rather thaninhibiting bone resorption, the compounds of structural formula Istimulate bone formation, acting preferentially on cortical bone, whichis responsible for a significant part of bone strength. The thickeningof cortical bone substantially contributes to a reduction in fracturerisk, especially fractures of the hip. The combination of the tissueselective androgen receptor modulators of structural formula I withresorption inhibitors such as estrogen, bisphosphonates, antiestrogens,SERMs, calcitonin, osteoclast integrin inhibitors HMG-CoA reductaseinhibitors, proton pump inhibitors, and cathepsin K inhibitors isparticularly useful because of the complementarity of the bone anabolicand antiresorptive actions.

[1010] Bone antiresportive agents are those agents which are known inthe art to inhibit the resorption of bone and include, for example,estrogen and estrogen derivatives which include steroidal compoundshaving estrogenic activity such as, for example, 17β-estradiol, estrone,conjugated estrogen (PREMARIN®), equine estrogen, 17β-ethynyl estradiol,and the like. The estrogen or estrogen derivative may be employed aloneor in combination with a progestin or progestin derivative. Nonlimitingexamples of progestin derivatives are norethindrone andmedroxy-progesterone acetate.

[1011] Bisphosphonates are also bone anti-resorptive agents.Bisphosphonate compounds may also be employed in combination with thecompound of structural formula I of the present invention include:

[1012] 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid,

[1013] N-methyl-4-amino-hydroxybutylidene-1,1-bisphosphonic acid,

[1014] 4-(N,N-dimethylamino-1-hydroxybutylidene-1,1-bisphosphonic acid,

[1015] 3-amino-1-hydroxypropylidene-1,1-bisphosphonic acid,

[1016] 3-(N,N-dimethylamino)-1-hydroxypropylidene-1,1-bisphosphonicacid,

[1017] 1-hydroxy-3-(N-methyl-N-pentylamino)propylidene-1,1-bisphosphonicacid,

[1018] 1-hydroxy-2-(3-pyridyl)ethylidene-1,1-bisphosphonic acid,

[1019] 4-(hydroxymethylene-1,1-bisphosphonic acid)piperidine,

[1020] (1-hydroxyethylidene)-bisphosphonate,

[1021] (dichloromethylene)-bisphosphonate,

[1022][1-hydroxy-2-imidazopyridin-(1,2-a)-3-ylethylidene]bisphosphonate,

[1023] (6-amino-1-hydroxyheylidene)bisphosphonate,

[1024] [1-hydroxy-2-(1H-imidazole-1-yl)ethylidene]bisphosphonate;

[1025] and their pharmaceutically acceptable salts. Especially preferredis alendronate, 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acidmonosodium salt, trihydrate.

[1026] Methods for the preparation of bisphosphonic acids may be foundin, e.g., U.S. Pat. Nos. 3,251,907; 3,422,137; 3,584,125; 3,940,436;3,944,599; 3,962,432; 4,054,598; 4,267,108; 4,327,039; 4,407,761;4,578,376; 4,621,077; 4,624,947; 4,746,654; 4,761,406; 4,922,077. Inparticular, methods for the preparation of4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid monosodium salttrihydrate may be found in U.S. Pat. No. 4,407,761 and 4,621,077.

[1027] Still further, antiestrogenic compounds such as raloxifene (see,e.g., U.S. Pat. No. 5,393,763) clomiphene, zuclomiphene, enclomiphene,nafoxidene, CI-680, CI-628, CN-55,945-27,Mer-25, U-11, 555A, U-100A, andsalts thereof, and the like (see, e.g., U.S. Pat. Nos. 4,729,999 and4,894,373) may be employed in combination with the compound ofstructural formula I in the methods and compositions of the presentinvention. These agents are also known as SERMs, or selective estrogenreceptor modulators, agents known in the art to prevent bone loss byinhibiting bone resorption via pathways believed to be similar to thoseof estrogens. These agents may beneficially be used in combination withthe compounds of the present invention to beneficially treat bonedisorders including osteoporosis. Such agents include, for example:tamoxifen, raloxifene, lasofoxifene, toremifene, azorxifene, EM-800,EM-652, TSE 424, clomiphene, droloxifene, idoxifene and levormeloxifene.(Goldstein, et al., A pharmacological review of selective oestrogenreceptor modulators. Human Reproduction Update, 6: 212-224, 2000, andLufkin, et al., The role of selective estrogen receptor modulators inthe prevention and treatment of Osteoporosis. Rheumatic Disease Clinicsof North America. 27 (1): 163-185, 2001.)

[1028] Osteoclast integrin inhibitors, also called vitronectininhibitors and αvβ3antagonists, suppress bone resorption and may beemployed in combination with the tissue selective androgen receptormodulators of structural formula I for the treatment of bone disordersincluding osteoporosis. Peptidyl as well as peptidomimetic antagonistsof the αvβ3 integrin receptor have been described both in the scientificand patent literature. For example, reference is made to W. J. Hoekstraand B. L. Poulter, Curr. Med. Chem. 5: 195-204, 1998 and referencescited therein; WO 95/32710; WO 95/37655; WO 97/01540; WO 97/37655; WO98/08840; WO 98/18460; WO 98/18461; WO 98/25892; WO 98/31359; WO98/30542; WO 99/15506; WO 99/15507; WO 00/03973; EP 853084; EP 854140;EP 854145; U.S. Pat. Nos. 5,204,350; 5,217,994; 5,639,754; 5,741,796;5,780,426; 5,929,120; 5,952,341; 6,017,925; and 6,048,861. Evidence ofthe ability of αvβ3 integrin receptor antagonists to prevent boneresorption in vitro and in vivo has been presented (V. W. Engleman, etal., “A Peptidomimetic Antagonist of the αvβ3 Integrin Inhibits BoneResorption In Vitro and Prevents Osteoporosis In Vivo,” J. Clin. Invest.99: 2284-2292, 1997; S. B. Rodan, et al., “A High Affinity Non-Peptideαvβ3 Ligand Inhibits Osteoclast Activity In Vitro and In Vivo,” J. BoneMiner. Res. 11: S289, 1996; J. F. Gourvest, et al., “Prevention ofOVX-Induced Bone Loss With a Non-peptidic Ligand of the αvβ3 VitronectinReceptor,” Bone 23: S612, 1998; M. W. Lark, et al., “An Orally ActiveVitronectin Receptor αvβ3 Antagonist Prevents Bone Resorption In Vitroand In Vivo in the Ovariectomized Rat,” Bone 23: S219, 1998). Other αvβ3antagonists are described in R. M. Keenan, et al., “Discovery of PotentNonpeptide Vitronectin Receptor (αvβ3) Antagonists,” J. Med. Chem. 40:2289-2292, 1997; R. M. Keenan, et al., “Benzimidazole Derivatives AsArginine Mimetics in 1,4-Benzodiazepine Nonpeptide Vitronectin Receptor(αvβ3) Antagonists,” Bioorg. Med. Chem. Lett. 8: 3165-3170, 1998; and R.M. Keenan, et al., “Discovery of an Imidazopyridine-Containing1,4-Benzodiazepine Nonpeptide Vitronectin Receptor (αvβ3) AntagonistWith Efficacy in a Restenosis Model,” Bioorg. Med. Chem. Lett. 8:3171-3176, 1998. Still other benzazepine, benzodiazepine andbenzocycloheptene αvβ3 integrin receptor antagonists are described inthe following patent publications: WO 96/00574, WO 96/00730, WO96/06087, WO 96/26190, WO 97/24119, WO 97/24122, WO 97/24124, WO98/14192, WO 98/15278, WO 99/05107, WO 99/06049, WO 99/15170, WO99/15178, WO 99/15506, and U.S. Pat. No. 6,159,964, and WO 97/34865.αvβ3 integrin receptor antagonists having dibenzocycloheptene,dibenzocycloheptane and dibenzoxazepine scaffolds have been described inWO 97/01540, WO 98/30542, WO 99/11626, WO 99/15508, WO 00/33838, U.S.Pat. Nos. 6,008,213, and 6,069,158. Other osteoclast integrin receptorantagonists incorporating backbone conformational ring constraints havebeen described in the patent literature. Published patent applicationsor issued patents disclosing antagonists having a phenyl constraintinclude WO 98/00395, WO 99/32457, WO 99/37621, WO 99/44994, WO99/45927,WO 99/52872, WO 99/52879, WO 99/52896, WO 00/06169, EP 0820,988, EP 0 820,991, U.S. Pat. Nos. 5,741,796; 5,773,644; 5,773,646;5,843,906; 5,852,210; 5,929,120; 5,952,381; 6,028,223; and 6,040,311.Published patent applications or issued patents disclosing antagonistshaving a monocyclic ring constraint include WO 99/26945, WO 99/30709, WO99/30713, WO 99/31099, WO 99/59992, WO 00/00486, WO 00/09503, EP 0796,855, EP 0 928,790, EP 0 928,793, U.S. Pat. Nos. 5,710,159;5,723,480; 5,981,546; 6,017,926; and 6,066,648. Published patentapplications or issued patents disclosing antagonists having a bicyclicring constraint include WO 98/23608, WO 98/35949, WO 99/33798, EP 0853,084, U.S. Patent Nos. 5,760,028; 5,919,792; and 5,925,655. Referenceis also made to the following reviews for additional scientific andpatent literature that concern alpha v integrin antagonists: M. E.Duggan, et al., “Ligands to the integrin receptor αvβ3, Exp. Opin. Ther.Patents, 10: 1367-1383, 2000; M. Gowen, et al., “Emerging therapies forosteoporosis,” Emerging Drugs, 5: 1-43, 2000; J. S. Kerr, et al., “Smallmolecule αv integrin antagonists: novel anticancer agents,” Exp. Opin.Invest. Drugs, 9: 1271-1291, 2000; and W. H. Miller, et al.,“Identification and in vivo efficacy of small-molecule antagonists ofintegrin αvβ3 (the vitronectin receptor),” Drug Discovery Today, 5:397-408, 2000.

[1029] Cathepsin K, formerly known as cathepsin O2, is a cysteineprotease and is described in PCT International Application PublicationNo. WO 96/13523, published May 9, 1996; U.S. Pat. No. 5,501,969, issuedMar. 3, 1996; and U.S. Pat. No. 5,736,357, issued Apr. 7, 1998, all ofwhich are incorporated by reference herein in their entirety. Cysteineproteases, specifically cathepsins, are linked to a number of diseaseconditions, such as tumor metastasis, inflammation, arthritis, and boneremodeling. At acidic pH's, cathepsins can degrade type-I collagen.Cathepsin protease inhibitors can inhibit osteoclastic bone resorptionby inhibiting the degradation of collagen fibers and are thus useful inthe treatment of bone resorption diseases, such as osteoporosis.

[1030] Members of the class of HMG-CoA reductase inhibitors, known asthe “statins,” have been found to trigger the growth of new bone,replacing bone mass lost as a result of osteoporosis (The Wall StreetJournal, Friday, Dec. 3, 1999, page B1). Therefore, the statins holdpromise for the treatment of bone resorption. Examples of HMG-CoAreductase inhibitors include statins in their lactonized or dihydroxyopen acid forms and pharmaceutically acceptable salts and estersthereof, including but not limited to lovastatin (see U.S. Pat. No.4,342,767); simvastatin (see U.S. Pat. No. 4,444,784); dihydroxyopen-acid simvastatin, particularly the ammonium or calcium saltsthereof; pravastatin, particularly the sodium salt thereof (see U.S.Pat. No. 4,346,227); fluvastatin particularly the sodium salt thereof(see U.S. Pat. No. 5,354,772); atorvastatin, particularly the calciumsalt thereof (see U.S. Pat. No. 5,273,995); cerivastatin, particularlythe sodium salt thereof (see U.S. Pat. No. 5,177,080), rosuvastatin,also known as ZD4522 (see U.S. Pat. No.5,260,440) and pitavastatin alsoreferred to as NK-104 or nisvastatin (see PCT international publicationnumber WO 97/23200).

[1031] Osteoclast vacuolar ATPase inhibitors, also called proton pumpinhibitors, may also be employed together with the tissue selectiveandrogen receptor modulator of structural formula I. The proton ATPasewhich is found on the apical membrane of the osteoclast has beenreported to play a significant role in the bone resorption process.Therefore, this proton pump represents an attractive target for thedesign of inhibitors of bone resorption which are potentially useful forthe treatment and prevention of osteoporosis and related metabolicdiseases (C. Farina, et al., “Selective inhibitors of the osteoclastvacuolar proton ATPase as novel bone resorption inhibitors,” DDT, 4:163-172, 1999).

[1032] The angiogenic factor VEGF has been shown to stimulate thebone-resorbing activity of isolated mature rabbit osteoclasts viabinding to its receptors on osteoclasts ( M. Nakagawa, et al., “Vascularendothelial growth factor (VEGF) directly enhances osteoclastic boneresorption and survival of mature osteoclasts,” FEBS Letters, 473:161-164, 2000). Therefore, the development of antagonists of VEGFbinding to osteoclast receptors, such as KDR/Flk-1 and Flt-1, mayprovide yet a further approach to the treatment or prevention of boneresorption.

[1033] Activators of the peroxisome proliferator-activated receptor-γ(PPARγ), such as the thiazolidinediones (TZD's), inhibit osteoclast-likecell formation and bone resorption in vitro. Results reported by R.Okazaki, et al. in Endocrinology, 140, pp 5060-5065, 1999 point to alocal mechanism on bone marrow cells as well as a systemic one onglucose metabolism. Nonlimiting examples of PPARγ activators includetroglitazone, pioglitazone, rosiglitazone, and BRL 49653.

[1034] Calcitonin may also be employed together with the tissueselective androgen receptor modulator of structural formula I.Calcitonin is preferentially administered as nasal spray. Azra, et al.,Calcitonin, 1996, In: J. P. Bilezikian, et al. Ed. Principles of BoneBiology, San Diego: Academic Press; and Silverman. Calcitonin,.Rheumatic Disease Clinics of North America 27:187-196, 2001).

[1035] Protein kinase inhibitors may also be employed together with thetissue selective androgen receptor modulator of structural formula I.Kinase inhibitors include those disclosed in WO 0117562 and are in oneembodiment selected from inhibitors of P-38. Specific embodiments ofP-38 inhibitors useful in the present invention include: SB 203580(Badger, et al., Pharmacological profile of SB 203580, a selectiveinhibitor of cytokine suppressive binding protein/p38 kinase, in animalmodels of arthritis, bone resorption, endotoxin shock and immunefunction, J. Pharmacol. Exp. Ther. 279: 1453-1461, 1996).

[1036] Osteoanabolic agents are those agents that are known in the artto build bone by increasing the production of the bone matrix. Suchosteoanabolic agents include, for example, the various forms ofparathyroid hormone (PTH) such as naturally occurring PTH (1-84), PTH(1-34), analogs thereof, native or with substitutions and particularlyparathyroid hormone subcutaneous injection. PTH has been found toincrease the activity of osteoblasts, the cells that form bone, therebypromoting the synthesis of new bone (Modern Drug Discovery, Vol. 3, No.8, 2000). In studies reported at the First World Congress onOsteoporosis held in Chicago in June 2000, women in combinedPTH-estrogen therapy exhibited a 12.8% increase in spinal bone mass anda 4.4% increase in total hip mass. Another study presented at the samemeeting showed that PTH could increase bone size as well as density. Aclinical trial of the effect of the human parathyroid hormone 1-34fragment [hPTH(1-34)] on postmenopausal osteoporotic women resulted in≧65% reduction in spine fractures and a 54% reduction in nonvertebralfractures, after a median of 22 months of treatment (J. M. Hock, Bone,27: 467-469, 2000 and S. Mohan, et al., Bone, 27: 471-478, 2000, andreferences cited therein). Thus, PTH and fragments thereof, such ashPTH(1-34), may prove to be efficacious in the treatment of osteoporosisalone or in combination with other agents, such as the tissue selectiveandrogen receptor modulators of the present invention.

[1037] Also useful in combination with the SARMs of the presentinvention are calcium receptor antagonists which induce the secretion ofPTH as described by Gowen, et al., in Antagonizing the parathyroidcalcium receptor stimulates parathyroid hormone secretion and boneformation in osteopenic rats, J Clin Invest. 105 :1595-604, 2000.

[1038] Growth hormone secretagogues, growth hormone, growth hormonereleasing hormone and insulin-like growth factor and the like are alsoosteoanabolic agents which may be employed with the compounds accordingto structural formula I for the treatment of osteoporosis.Representative growth hormone secretagogues are disclosed in U.S. Pat.No. 3,239,345; 4,036,979; 4,411,890; 5,206,235; 5,283,241; 5,284,841;5,310,737; 5,317,017; 5,374,721; 5,430,144; 5,434,261; 5,438,136;5,494,919; 5,494,920; 5,492,916; 5,536,716; EPO Patent Pub. No.0,144,230; EPO Patent Pub. No. 0,513,974; PCT Patent Pub. No. WO94/07486; PCT Patent Pub. No. WO 94/08583; PCT Patent Pub. No. WO94/11012; PCT Patent Pub. No. WO 94/13696; PCT Patent Pub. No. WO94/19367; PCT Patent Pub. No. WO 95/03289; PCT Patent Pub. No. WO95/03290; PCT Patent Pub. No. WO 95/09633; PCT Patent Pub. No. WO95/11029; PCT Patent Pub. No. WO 95/12598; PCT Patent Pub. No. WO95/13069; PCT Patent Pub. No. WO 95/14666; PCT Patent Pub. No. WO95/16675; PCT Patent Pub. No. WO 95/16692; PCT Patent Pub. No. WO95/17422; PCT Patent Pub. No. WO 95/17423; PCT Patent Pub. No. WO95/34311; PCT Patent Pub. No. WO 96/02530; Science, 260, 1640-1643, Jun.11, 1993; Ann. Rep. Med. Chem., 28, 177-186 (1993); Bioorg. Med. Chem.Ltrs., 4(22), 2709-2714, 1994; and Proc. Natl. Acad. Sci. USA 92,7001-7005, July 1995.

[1039] Insulin-like growth factor (IGF) may also be employed togetherwith the tissue selective androgen receptor modulator of structuralformula I. Insulin-like growth factors may be selected from Insulin-likeGrowth Factor I, alone or in combination with IGF binding protein 3 andIGF II. (Johannson and Rosen, The IGFs as potential therapy formetabolic bone diseases, 1996, In: Bilezikian, et. al. Ed. Principles ofBone Biology. San Diego: Academic Press; and Ghiron, et al., Effects ofrecombinant insulin-like growth factor-I and growth hormone on boneturnover in elderly women, J Bone Miner Res. 10 :1844-52, 1995).

[1040] Bone morphogenic protein (BMP) may also be employed together withthe tissue selective androgen receptor modulator of structural formulaI. Bone morphogenic protein includes BMP 2, 3, 5, 6, 7, as well asrelated molecules TGF beta and GDF 5. (Rosen, et al., Bone morphogeneticproteins. 1996. In: J. P. Bilezikian, et. al. Ed. Principles of BoneBiology, San Diego: Academic Press; and Wang E A, Bone morphogeneticproteins (BMPs): therapeutic potential in healing bony defects. TrendsBiotechnol. 11 :379-83, 1993)

[1041] Inhibitors of BMP antagonism may also be employed together withthe tissue selective androgen receptor modulator of structural formulaI. BMP antagonist inhibitors are in one embodiment selected frominhibitors of the BMP antagonists SOST, noggin, chordin, gremlin, anddan (Massague and Chen Controlling TGF-beta signaling, Genes Dev. 14:627-44, 2000; Aspenberg, et al., The bone morphogenetic proteinsantagonist Noggin inhibits membranous ossification, J Bone Miner Res. 16:497-500, 2001; Brunkow, et al., Bone dysplasia sclerosteosis resultsfrom loss of the SOST gene product, a novel cystine knot-containingprotein, Am J Hum Genet. 68: 577-89, 2001).

[1042] Prostaglandin derivatives may also be employed together with thetissue selective androgen receptor modulator of structural formula I.Prostaglandin derivatives are in one embodiment selected from agonistsof prostaglandin receptor EP1, EP2, EP4, FP and IP or a derivativethereof. Pilbeam, et al., Prostaglandins and bone metabolism, 1996, In:Bilezikian, et al. Ed. Principles of Bone Biology. San Diego: AcademicPress; Weinreb, et al., Expression of the prostaglandin E(2) (PGE(2))receptor subtype EP(4) and its regulation by PGE(2) in osteoblastic celllines and adult rat bone tissue(1), Bone. 28(3):275-81, 2001.

[1043] Fibroblast growth factors may also be employed together with thetissue selective androgen receptor modulator of structural formula I.Fibroblast growth factors include aFGF, bFGF and related peptides withFGF activity. Hurley Florkiewicz; Fibroblast growth factor and vascularendothelial growth factor families. 1996. In: J. P. Bilezikian, et. al.Ed. Principles of Bone Biology. San Diego: Academic Press.

[1044] In addition to bone resorption inhibitors and osteoanabolicagents, there are also other agents known to be beneficial for theskeleton through the mechanisms which are not precisely defined. Theseagents may also be favorably combined with the tissue selective androgenreceptor modulator of structural formula I

[1045] Vitamin D and Vitamin D derivatives may also be employed togetherwith the tissue selective androgen receptor modulator of structuralformula I. Vitamin D and Vitamin D derivatives include: natural vitaminD, 25-OH-vitamin D3, 1α,25(OH)2 vitamin D3, 1α-OH-vitamin D3,1α-OH-vitamin D2, dihydrotachysterol, 26,27-F6-1α, 25(OH)2 vitamin D3,19-nor-1α, 25(OH)2 vitamin D3, 22-oxacalcitriol, calcipotriol, 1α,25(OH)2-16-ene-23-yne-vitamin D3 (Ro 23-7553), EB1089, 20-epi-1α,25(OH)2 vitamin D3, KH1060, ED71, 1α, 24(S)-(OH)2 vitamin D3, 1α,24(R)-(OH)2 vitamin D3. (Jones G. Pharmacological mechanisms oftherapeutics: vitamin D and analogs. 1996. In: J. P. Bilezikian, et. al.Ed. Principles of Bone Biology. San Diego: Academic Press).

[1046] Vitamin K and Vitamin K derivatives may also be employed togetherwith the tissue selective androgen receptor modulator of structuralformula I. Vitamin K and Vitamin K derivatives include: menatetrenone(vitamin K2). Shiraki, et al., Vitamin K2 (menatetrenone) effectivelyprevents fractures and sustains lumbar bone mineral density inosteoporosis, J Bone Miner Res. 15 : 515-21.

[1047] Soy isoflavones including ipriflavone may be employed togetherwith the tissue selective androgen receptor modulator of structuralformula I.

[1048] Fluoride salts, including sodium fluoride (NaF) or monosodiumfluorophosphate (MFP) may also be employed together with the tissueselective androgen receptor modulator of structural formula I Dietarycalcium supplements may also be employed together with the tissueselective androgen receptor modulator of structural formula I. Dietarycalcium supplements include calcium carbonate, calcium citrate andnatural calcium salts (Heaney, Calcium, 1996, In: J. P. Bilezikian, et.al. Ed. Principles of Bone Biology. San Diego: Academic Press).

[1049] Daily dosage ranges for bone resorption inhibitors, osteoanabolicagents and other agents which may be used to benefit the skeleton whenused in combination with the compounds of structural formula I are thosewhich are known in the art. In such combinations, generally the dailydosage range for the tissue selective androgen receptor modulator ofstructural formula I is 0.01 to 1000 mg per adult human per day, morepreferably from 0.1 to 200 mg/day. However, adjustments to decrease thedose of each agent may be made due to the increased efficacy of thecombined agent.

[1050] In particular, when a bisphosphonate is employed, dosages of 2.5to 100 mg/day (measured as the free bisphosphonic acid) are appropriatefor treatment, more preferably 5 to 20 mg/day, especially about 10mg/day. Prophylactically, doses of about 2.5 to about 10 mg/day andespecially about 5 mg/day should be employed. For reduction inside-effects, it may be desirable to administer the combination of thecompound of structural formula I and the bisphosphonate once a week. Foronce weekly administration, doses of about 15 mg to 700 mg per week ofbisphosphonate and 0.07 to 7000 mg of the compound of structural formulaI may be employed, either separately, or in a combined dosage form. Thecompound of strucutral formula I may be favorably administered in acontrolled-release delivery device, particularly for once weeklyadministration.

[1051] For the treatment of atherosclerosis, hypercholesterolemia,hyperlipidemia, the compounds of structural formula I may be effectivelyadministered in combination with one or more additional active agents.The additional active agent or agents can be lipid altering compoundssuch as HMG-CoA reductase inhibitors, or agents having otherpharmaceutical activities, or agents that have both lipid-alteringeffects and other pharmaceutical activities. Examples of HMG-CoAreductase inhibitors include statins in their lactonized or dihydroxyopen acid forms and pharmaceutically acceptable salts and estersthereof, including but not limited to lovastatin (see U.S. Pat. No.4,342,767); simvastatin (see U.S. Pat. No. 4,444,784); dihydroxyopen-acid simvastatin, particularly the ammonium or calcium saltsthereof; pravastatin, particularly the sodium salt thereof (see U.S.Pat. No. 4,346,227); fluvastatin particularly the sodium salt thereof(see U.S. Pat. No. 5,354,772); atorvastatin, particularly the calciumsalt thereof (see U.S. Pat. No. 5,273,995); cerivastatin, particularlythe sodium salt thereof (see U.S. Pat. No. 5,177,080), and nisvastatinalso referred to as NK-104 (see PCT international publication number WO97/23200). Additional active agents which may be employed in combinationwith a compound of structural formula I include, but are not limited to,HMG-CoA synthase inhibitors; squalene epoxidase inhibitors; squalenesynthetase inhibitors (also known as squalene synthase inhibitors),acyl-coenzyme A: cholesterol acyltransferase (ACAT) inhibitors includingselective inhibitors of ACAT-1 or ACAT-2 as well as dual inhibitors ofACAT1 and -2; microsomal triglyceride transfer protein (MTP) inhibitors;probucol; niacin; cholesterol absorption inhibitors such as SCH-58235also known as ezetimibe and 1-(4-fluorophenyl)-3(R)-683(S)-(4-fluorophenyl)-3-hydroxypropyl)69-4(S)-(4-hydroxyphenyl)-2-azetidinone, which is described in U.S. Pat.No.'s 5,767,115 and 5,846,966; bile acid sequestrants; LDL (low densitylipoprotein) receptor inducers; platelet aggregation inhibitors, forexample glycoprotein IIb/IIIa fibrinogen receptor antagonists andaspirin; human peroxisome proliferator activated receptor gamma (PPARγ)agonists including the compounds commonly referred to as glitazones forexample troglitazone, pioglitazone and rosiglitazone and, includingthose compounds included within the structural class known asthiazolidinediones as well as those PPARγ agonists outside thethiazolidinedione structural class; PPARα agonists such as clofibrate,fenofibrate including micronized fenofibrate, and gemfibrozil; PPAR dualα/γ agonists; vitamin B₆ (also known as pyridoxine) and thepharmaceutically acceptable salts thereof such as the HCl salt; vitaminB₁₂ (also known as cyanocobalamin); folic acid or a pharmaceuticallyacceptable salt or ester thereof such as the sodium salt and themethylglucamine salt; anti-oxidant vitamins such as vitamin C and E andbeta carotene; beta-blockers; angiotensin II antagonists such aslosartan; angiotensin converting enzyme inhibitors such as enalapril andcaptopril; calcium channel blockers such as nifedipine and diltiazam;endothelian antagonists; agents such as LXR ligands that enhance ABC1gene expression; bisphosphonate compounds such as alendronate sodium;and cyclooxygenase-2 inhibitors such as rofecoxib and celecoxib as wellas other agents known to be useful in the treatment of these conditions.

[1052] Daily dosage ranges for HMG-CoA reductase inhibitors when used incombination with the compounds of structural formula I correspond tothose which are known in the art. Similarly, daily dosage ranges for theHMG-CoA synthase inhibitors; squalene epoxidase inhibitors; squalenesynthetase inhibitors (also known as squalene synthase inhibitors),acyl-coenzyme A: cholesterol acyltransferase (ACAT) inhibitors includingselective inhibitors of ACAT-1 or ACAT-2 as well as dual inhibitors ofACAT1 and -2; microsomal triglyceride transfer protein (MTP) inhibitors;probucol; niacin; cholesterol absorption inhibitors including ezetimibe;bile acid sequestrants; LDL (low density lipoprotein) receptor inducers;platelet aggregation inhibitors, including glycoprotein IIb/IIafibrinogen receptor antagonists and aspirin; human peroxisomeproliferator activated receptor gamma (PPARγ) agonists; PPARα agonists;PPAR dual α/γ agonists; vitamin B_(6;) vitamin B₁₂; folic acid;anti-oxidant vitamins; beta-blockers; angiotensin II antagonists;angiotensin converting enzyme inhibitors; calcium channel blockers;endothelian antagonists; agents such as LXR ligands that enhance ABC1gene expression; bisphosphonate compounds; and cyclooxygenase-2inhibitors also corespond to those which are known in the art, althoughdue to the combined action with the compounds of structural formula I,the dosage may be somewhat lower when administered in combination.

[1053] In accordance with the method of the present invention, theindividual components of the combination can be administered separatelyat different times during the course of therapy or concurrently individed or single combination forms. The instant invention is thereforeto be understood as embracing all such regimes of simultaneous oralternating treatment and the term “administering” is to be interpretedaccordingly. It will be understood that the scope of combinations of thecompounds of this invention with other agents useful for treatingdiseases caused by androgen deficiency or that can be ameliorated byaddition of androgen.

[1054] The following examples are provided to further illustrate detailsfor the preparation and use of the compounds of the present invention.The examples are not intended to be limitations on the scope of theinstant invention in any way, and they should not be so construed.Furthermore, the compounds described in the following examples are notto be construed as forming the only genus that is considered as theinvention, and any combination of the compounds or their moieties mayitself form a genus. Those skilled in the art will readily understandthat known variations of the conditions and processes of the followingpreparative procedures can be used to prepare these compounds. Alltemperatures are in degrees Celsius unless noted otherwise.

[1055] Abbreviations: Ac represents acetyl; AR is the androgen receptor;cPr is cyclopropyl; ddWater is distilled, deionized water; DMEM isDulbecco's Modified Eagle Media; DMF is dimethyl formamide; EDTA isethylenediaminetetraacetic acid; EGTA is ethylenebis(oxyethylenenitrolo) tetraacetic acid; Et represents ethyl; FCS isfetal calf serum; HAP is hydroxylapatite; hAR is the human androgenreceptor; Me is methyl; MEM is Minimum Essential Media; min. is minute;NMM is N-methyl morpholine; PBS is phosphate buffered saline (8 g NaCl,0.2 g KCl, 1.44 g Na₂HPO₄, 0.24 KH₂PO₄ dissolve into H₂O to make 1 L andadjust pH to 7.4 with HCl); Ph is phenyl; pQCT is peripheralquantitative computer tomography; R1881 is methyltrienolone, an androgenreceptor agonist; RhAR is the rhesus androgen receptor; SARM is a tissueselective androgen receptor modulator; SEAP is secreted alkalinephosphatase; TAC is triamcinolone acetonide; THF is tetrahydrofuran.

Preparatory Example 1 Methyl3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate 1

[1056] Compound 1 was prepared as described by Rasmusson, et al., J.Med. Chem., 29, 2298, 1986.

Preparatory Example 23-Oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxylic acid 3A

[1057] Compound 3A was prepared as described by Tolman et al J. SteroidBiochem. Molec. Biol., 60: 303-309, 1997.

Preparatory Example 33-Oxo-4-ethyl-4-aza-5α-androst-1-ene-17βD-carboxylic acid 3B

[1058] Compound 1 (5.0 g, 15.1 mmol) was dissolved in 60 mL of THF atroom temperature and NaH (665 mg, 16.6 mmol; 60% dispersion in mineraloil) added. After 30 minutes, EtI (1.45 mL, 18.1 mL) was added and themixture was heated at 60° C. for 16 hours. A further 200 mg NaH and 1 mLEtI was added and heating was continued for 24 hours. The mixture wascooled, poured onto ice-water and extracted 2×EtOAc. The organic layerswere washed with water then brine, dried (MgSO₄) and evaporated to givea solid. This solid was swished with ether/hexane (1:1) and filtered togive methyl 3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxylate 2B. Theester 2B (4.1 g, 11.4 mmol) was dissolved in dioxane (120 mL), treatedwith 1N LiOH (35 mL, 35 mmol) and heated to reflux for 16 hours. Thesolution was cooled, acidified with 3N HCl and extracted 4×CH₂Cl₂. Afterdrying (MgSO4) the solvent was removed to give the title compound 3B asa white solid. Mass spectrum: (M+H)⁺ found 346.0.

Preparatory Example 43-Oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxylic acid 3C

[1059] The title compound 3C was prepared as a white solid using themethod described for the preparation of acid 3B but using allyl bromideas the alkylating agent. Mass spectrum: (M+H)⁺ found 359.0

Preparatory Example 53-Oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxylic acid 3D

[1060] The title compound 3D was prepared as a white solid using themethod described for the preparation of acid 3B but using benzyl bromideas the alkylating agent. Mass spectrum: (M+H)³⁰ found 408.0

Preparatory Example 63-Oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxylic acid 3E

[1061] Compound 1 (5.0 g, 15.1 mmol), K₂CO₃ (4.6 g, 30.2 mmol),iodobenzene (6.15 g, 30.2 mmol) and CuI (287 mg, 1.5 mmol) weredissolved in 30 mL of DMF at room temperature and then heated at refluxfor 16 hours. A further 2 ML iodobenzene, 500 mg CuI and 5 g K2CO3 wereadded and heating was continued for 24 hours. Another addition ofreagents (2 mL iodobenzene, 500 mg CuI and 5 g K₂CO₃) was made and themixture stirred a further 24 hours at reflux. The mixture was cooled,filtered and partitioned between water and EtOAc. The organic layer waswashed with water then brine, dried (MgSO4) and evaporated to givemethyl 3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17p-carboxylate 2E (5.0 g)as a tan solid. The ester 2E (4.9 g, 12 mmol) was dissolved in dioxane(150 mL), treated with 1N LiOH (50 mL, 50 mmol) and heated to reflux for16 hours. The solution was cooled, acidified with 3N HCl and extracted4×CH₂Cl_(2.) After drying (MgSO4) the solvent was removed to give thetitle compound 3E as an off-white solid. Mass spectrum: M+30 H)⁺ found394.2379.

Preparatory Example 73-Oxo-4-methyl-4-aza-5α-androst-5-ene-170-carboxylic acid 8A

[1062] Compound 8A was prepared as described by Rasmusson, et al., inU.S. Pat. 4,220,775.

Preparatory Example 83-Oxo-4-cyclopropyl-4-aza-5αc-androst-5-ene-17,-carboxylic acid 8B

[1063] Compound 7 (5 g, 15.5 mmol; prepared as described by Rasmusson,et al., in U.S. Pat. No. 4,220,775), cyclopropylamine (6.2 g, 189 mmol)and ethylene glycol (30 mL) were heated at 180° C. for 1 hour. Thesolution was cooled, poured into 1N HCl and water and the resultingprecipitate removed by filtration. The filtrate was extracted 3×EtOAc,dried (MgSO4) and the solvent removed in vacuo to give a red oil. Columnchromatography (silica gel; hexane/EtOAc 4:1 rising to 1:2 then pureEtOAc) afforded the title compound 8B as a tan solid. Mass spectrum:M+30 H)⁺ found 358.1.

EXAMPLE 1

[1064] Preparation of 4-Substituted3-oxo-4-aza-5α-androst-1-ene-17β-carboxamides (5)

[1065] These compounds were prepared by one of 2 methods (see Scheme 2)from 4-substituted 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylic acids 3according to the procedures described by Tolman, et al., J. SteroidBiochem. Molec. Biol., 1997, 60, 303-309 and Rasmusson, et al., J. Med.Chem., 1986, 29, 2298.

[1066] Method A. Preparation of 5 requires the formation of thethiopyridyl activated ester 4 followed by coupling with the desiredamine with silver triflate.

[1067] Method B. Direct coupling of the acid 3 with EDC, HOAT (or HOBT),an organic base and the desired amine to give 5. TABLE 1 4-Substituted3-oxo-4-aza-5α-androst-1-ene-17β-carboxamides Compound (M+H)⁺ No.Compound Name observed 1-1N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β- 407.2682carboxamide 1-2 N-(2-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-441.2331 ene-17β-carboxamide 1-3N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α- 475.2579androst-1-ene-17β-carboxamide 1-4N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 425.2609ene-17β-carboxamide 1-5N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 437.2795ene-17β-carboxamide 1-6N-(2-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene- 483.300317β-carboxamide 1-7N-(4-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene- 483.300917β-carboxamide 1-8N-(3-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene- 483.305317β-carboxamide 1-9N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 421.2857ene-17β-carboxamide 1-10N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 437.2793ene-17β-carboxamide 1-11N-(3-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 441.2299ene-17β-carboxamide 1-12N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α- 475.2567androst-1-ene-17β-carboxamide 1-13N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α- 491.2509androst-1-ene-17β-carboxamide 1-14N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 421.2856ene-17β-carboxamide 1-15N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 437.2791ene-17β-carboxamide 1-16N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 425.2607ene-17β-carboxamide 1-17N-(2-methyl-4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4- 505.2662aza-5α-androst-1-ene-17β-carboxamide 1-18N-(4-methoxy-3-trifluoromethylphenyl)-3-oxo-4-methyl-4- 505.2665aza-5α-androst-1-ene-17β-carboxamide 1-19N-(4-chloro-3-trifluoromethylphenyl)-3-oxo-4-methyl-4- 509.2175aza-5α-androst-1-ene-17β-carboxamide 1-20N-(2,4-dimethoxyphenyl)-3-oxo-4-methyl-4-aza-5α- 467.2906androst-1-ene-17β-carboxamide 1-21N-(3-bromo-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α- 499.1950androst-1-ene-17β-carboxamide 1-22N-(2,2,2-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst- 413.24291-ene-17β-carboxamide 1-23N-(2-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α- 489.2756androst-1-ene-17β-carboxamide 1-24N-(butyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β- 387.3009carboxamide 1-25 N-(5-methyl-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-422.2818 androst-1-ene-17β-carboxamide 1-26N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α- 475.2603androst-1-ene-17β-carboxamide 1-27N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 425.2617ene-17β-carboxamide 1-28N-(4-bromo-2-trifluoromethylphenyl)-3-oxo-4-methyl-4- 553.1724aza-5α-androst-1-ene-17β-carboxamide 1-29N-(4-chloro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4- 509.2223aza-5α-androst-1-ene-17β-carboxamide 1-30N-(2,4-dichlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst- 475.19551-ene-17β-carboxamide 1-31N-(3-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 432.2670ene-17β-carboxamide 1-32N-(4-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 432.2657ene-17β-carboxamide 1-33N-(5-fluoro-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst- 426.25711-ene-17β-carboxamide 1-34N-(5-chloro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α- 455.2496androst-1-ene-17β-carboxamide 1-35N-(benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β- 421.2845carboxamide 1-36 N-((S)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-435.2995 1-ene-17β-carboxamide 1-37N-((R)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst- 435.29951-ene-17β-carboxamide 1-38N-(2-phenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene- 435.299217β-carboxamide 1-39N-(1-(3-phenylpropyl))-3-oxo-4-methyl-4-aza-5α-androst- 449.31431-ene-17β-carboxamide 1-40N-(3-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 422.2804ene-17β-carboxamide 1-41N-(2-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 439.2741ene-17β-carboxamide 1-42N-(2-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 497.3144ene-17β-carboxamide 1-43N-(3-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 497.3144ene-17β-carboxamide 1-44N-(3-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 455.2438ene-17β-carboxamide 1-45N-(4-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 455.2436ene-17β-carboxamide 1-46N-(3-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 451.2938ene-17β-carboxamide 1-47N-(2-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 451.2938ene-17β-carboxamide 1-48N-(cyclohexylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 427.3308ene-17β-carboxamide 1-49N-(3-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene- 466.268617β-carboxamide 1-50N-(2-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 435.2990ene-17β-carboxamide 1-51N-(3-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 435.2992ene-17β-carboxamide 1-52N-(4-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 435.2992ene-17β-carboxamide 1-53N-(3-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α- 489.2706androst-1-ene-17β-carboxamide 1-54N-(3-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 439.2739ene-17β-carboxamide 1-55N-(4-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 439.2739ene-17β-carboxamide 1-56N-(2-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 455.2441ene-17β-carboxamide 1-57N-(4-methoxylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 451.2938ene-17β-carboxamide 1-58N-(4-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 441.2297ene-17β-carboxamide 1-59N-((R)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α- 449.3155androst-1-ene-17β-carboxamide 1-60N-((S)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α- 449.3146androst-1-ene-17β-carboxamide 1-61N-(3-(1-pyrrolidin-2-one)-1-propyl)-3-oxo-4-methyl-4-aza- 456.32155α-androst-1-ene-17β-carboxamide 1-62N-(2-furanylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 411.2647ene-17β-carboxamide 1-63N-(1-naphthylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 471.3014ene-17β-carboxamide 1-64N-(2-(4-imidazoylethyl))-3-oxo-4-methyl-4-aza-5α- 425.2917androst-1-ene-17β-carboxamide 1-65N-(2-(3-indolylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1- 474.3124ene-17β-carboxamide 1-66N-(5-indolyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β- 446.2802carboxamide 1-67 N-((1,2-methylenedioxy)-4-benzyl)-3-oxo-4-methyl-4-aza-465.2763 5α-androst-1-ene-17β-carboxamide 1-68N-(1,2-diphenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 511.3323ene-17β-carboxamide 1-69N-(2-(1-hydroxy-1-phenylethyl))-3-oxo-4-methyl-4-aza- 451.29375α-androst-1-ene-17β-carboxamide 1-70N-(2-(2-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α- 469.2636androst-1-ene-17β-carboxamide 1-71N-(3-(1-imidazolyl)-1-propyl)-3-oxo-4-methyl-4-aza-5α- 439.3063androst-1-ene-17β-carboxamide 1-72N-(2-(2-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α- 465.3130androst-1-ene-17β-carboxamide 1-73N-(2-methoxyethyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 389.2808ene-17β-carboxamide 1-74N-(4-fluoro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4- 493.2519aza-5α-androst-1-ene-17β-carboxamide 1-75N-(2,4-difluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst- 443.25241-ene-17β-carboxamide 1-76N-(4-fluoro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α- 439.2771androst-1-ene-17β-carboxamide 1-77N-(4-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 499.3002ene-17β-carboxamide 1-78N-(2-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 499.2997ene-17β-carboxamide 1-79N-(3-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 499.2981ene-17β-carboxamide 1-80N-(3,4-difluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst- 457.26641-ene-17β-carboxamide 1-81N-(4-dimethylaminobenzyl)-3-oxo-4-methyl-4-aza-5α- 464.3289androst-1-ene-17β-carboxamide 1-82N-(2-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene- 447.299817β-carboxamide 1-83 N-(2-benzamidazolemethyl)-3-oxo-4-methyl-4-aza-5α-461.2916 androst-1-ene-17β-carboxamide 1-84N-(1-(4-phenylbutyl))-3-oxo-4-methyl-4-aza-5α-androst-1- 463.3340ene-17β-carboxamide 1-85N-(3,5-dimethoxybenzyl)-3-oxo-4-methyl-4-aza-5α- 481.3068androst-1-ene-17β-carboxamide 1-86N-(2-(2-pyridinylethyl)-3-oxo-4-methyl-4-aza-5α-androst- 436.29621-ene-17β-carboxamide 1-87N-(2-methyl-5-pyrazolemethyl)-3-oxo-4-methyl-4-aza-5α- 437.2912androst-1-ene-17β-carboxamide 1-88N-(2-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 422.2811ene-17β-carboxamide 1-89N-(2-(2-thiophenylethyl)-3-oxo-4-methyl-4-aza-5α- 441.2573androst-1-ene-17β-carboxamide 1-90N-(1-(1-naphthyl)-1(R)-ethyl)-3-oxo-4-methyl-4-aza-5α- 485.3171androst-1-ene-17β-carboxamide 1-91N-(2-(3-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α- 469.2641androst-1-ene-17β-carboxamide 1-92N-(2-(2-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α- 453.2921androst-1-ene-17β-carboxamide 1-93N-(2-(4-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α- 453.2923androst-1-ene-17β-carboxamide 1-94N-(4-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene- 466.271717β-carboxamide, 1-95N-(2-(3-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α- 453.2912androst-1-ene-17β-carboxamide 1-96N-(2-(3,4-methylenedioxyphenylethyl))-3-oxo-4-methyl-4- 479.2921aza-5α-androst-1-ene-17β-carboxamide 1-97N-(2-thiophenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst- 427.24241-ene-17β-carboxamide 1-98N-(2-(4-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α- 465.3128androst-1-ene-17β-carboxamide 1-99N-(2-aminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1- 436.2966 ene-17β-carboxamide, 1-100 N-(2-(4-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-469.2642 androst-1-ene-17β-carboxamide 1-101 N-((1S,2R)2-hydroxy-1-indanyl)-3-oxo-4-methyl-4-aza- 463.29755α-androst-1-ene-17β-carboxamide 1-102N-(2-dimethylaminoethyl)-3-oxo-4-methyl-4-aza-5α- 402.3143androst-1-ene-17β-carboxamide 1-103N-(phenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β- 421.2859carboxamide 1-104N-(2-chlorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene- 455.246317β-carboxamide 1-105N-(2-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α- 489.2716androst-1-ene-17β-carboxamide 1-106N-(2-trifluoromethoxyphenyl)-3-oxo-4-ethyl-4-aza-5α- 505.2673androst-1-ene-17β-carboxamide 1-107N-(2-methoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1- 451.2953ene-17β-carboxamide 1-108N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β- 435.3006carboxamide 1-109N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene- 439.275317β-carboxamide 1-110N-(1,1,1-trifluoroethyl)-3-oxo-4-ethyl-4-aza-5α-androst-1- 427.2579ene-17β-carboxamide 1-111N-(2-propyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β- 387.3011carboxamide 1-112N-(2-biphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β- 497.3162carboxamide 1-113N-(2-acetylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene- 463.296317β-carboxamide 1-114N-(3-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α- 489.2726androst-1-ene-17β-carboxamide 1-115N-(2-pyridinyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β- 422.2835carboxamide 1-116N-(3-pyridinyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β- 422.2828carboxamide 1-117 N-(2-methylsulfonylphenyl)-3-oxo-4-ethyl-4-aza-5α-499.2638 androst-1-ene-17β-carboxamide 1-118N-(2-methylsulfoxyphenyl)-3-oxo-4-ethyl-4-aza-5α- 483.2668androst-1-ene-17β-carboxamide 1-119N-(phenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β- 433.2847carboxamide 1-120N-(2-chlorophenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene- 467.246617β-carboxamide 1-121N-(2-trifluoromethylphenyl)-3-oxo-4-allyl-4-aza-5α- 501.2721androst-1-ene-17β-carboxamide 1-122N-(3-methylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene- 447.301517β-carboxamide 1-123N-(2-methylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene- 447.301317β-carboxamide 1-124N-(2-cyanophenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene- 458.280317β-carboxamide 1-125N-(2-benzoylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1- 537.3120ene-17β-carboxamide 1-126N-(1,1,1-trifluoroethyl)-3-oxo-4-allyl-4-aza-5α-androst-1- 439.2559ene-17β-carboxamide 1-127N-(phenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β- 483.3010carboxamide 1-128 N-(2-chlorophenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-517.2614 ene-17β-carboxamide 1-129N-(2-trifluoromethylphenyl)-3-oxo-4-benzyl-4-aza-5α- 551.2877androst-1-ene-17β-carboxamide 1-130N-(phenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β- 469.2842carboxamide 1-131 N-(2-trifluoromethylphenyl)-3-oxo-4-phenyl-4-aza-5α-537.2729 androst-1-ene-17β-carboxamide 1-132N-(2-chlorophenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1- 503.2460ene-17β-carboxamide

EXAMPLE 2 Preparation of 4-Substituted3-oxo-4-aza-5α-androstane-17β-carboxamides (6)

[1068] These compounds may be prepared from 4-substituted3-oxo-4-aza-5α-androst-5-ene-17β-carboxylic acids (8) according to theprocedures described by Rasmusson, et al., in U.S. Pat. No. 4,220,775.Alternatively, catalytic reduction of 4-substituted3-oxo-4-aza-5α-androst-1-ene-17β-carboxamides 5 using palladium oncarbon, hydrogen gas in EtOAc and EtOH affords the saturated analogs 6.TABLE 2 4-Substituted 3-oxo-4-aza-5α-androstane-17β-carboxamidesCompound (M+H)⁺ No. Compound Name observed 2-1N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane- 423.302617β-carboxamide 2-2 N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-439.2943 androstane-17β-carboxamide 2-3N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α- 493.2701androstane-17β-carboxamide 2-4N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane- 423.302917β-carboxamide 2-5 N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-439.2971 androstane-17β-carboxamide 2-6N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androstane- 427.277517β-carboxamide 2-7 N-(phenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-423.3012 carboxamide 2-8N-(2-methoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane- 453.311317β-carboxamide 2-9 N-(2-propyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-389.3166 carboxamide 2-10N-(2-biphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β- 499.3323carboxamide 2-11 N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-437.3165 carboxamide 2-12N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androstane- 441.291317β-carboxamide 2-13 N-(1,1,1-trifluoroethyl)-3-oxo-4-ethyl-4-aza-5α-429.2737 androstane-17β-carboxamide 2-14N-(4-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α- 491.2886androstane-17β-carboxamide

EXAMPLE 3 Preparation of 4-substituted3-oxo-4-aza-5α-androst-5-ene-17β-carboxamides (9)

[1069] These compounds were prepared by one of 2 methods (see Schemes 2and 3) from 4-substituted 3-oxo-4-aza-5α-androst-5-ene-17β-carboxylicacids 8 according to the procedures described by Tolman, et al., J.Steroid Biochem. Molec. Biol., 1997, 60, 303-309 and Rasmusson, et al.,J. Med. Chem., 1986, 29, 2298.

[1070] Method A. Preparation of 9 requires the formation of thethiopyridyl activated ester followed by coupling with the desired aminewith silver triflate.

[1071] Method B. Direct coupling of the acid 8 with EDC, HOAT (or HOBT),an organic base and the desired amine to give 9. TABLE 3 4-Substituted3-oxo-4-aza-5α-androst-5-ene-17β-carboxamides Compound (M+H)⁺ No.Compound Name observed 3-1N-(1,1,1-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst- 413.23975-ene-17β-carboxamide 3-2N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β- 407.2691carboxamide 3-3 N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-475.2571 androst-5-ene-17β-carboxamide 3-4N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α- 475.2542androst-5-ene-17β-carboxamide 3-5N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α- 475.2538androst-5-ene-17β-carboxamide 3-6N-(2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5- 421.2861ene-17β-carboxamide 3-7N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5- 421.2834ene-17β-carboxamide 3-8N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5- 421.2862ene-17β-carboxamide 3-9N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5- 425.2580ene-17β-carboxamide 3-10N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5- 425.2563ene-17β-carboxamide 3-11N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5- 425.2579ene-17β-carboxamide 3-12N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst- 437.27925-ene-17β-carboxamide 3-13N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst- 437.27735-ene-17β-carboxamide 3-14N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst- 437.27745-ene-17β-carboxamide 3-15N-(phenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene- 433.284117β-carboxamide 3-16N-(2-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza- 501.27185α-androst-5-ene-17β-carboxamide 3-17N-(2-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α- 451.2752androst-5-ene-17β-carboxamide 3-18N-(3-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α- 467.2474androst-5-ene-17β-carboxamide 3-19N-(3-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza- 501.27235α-androst-5-ene-17β-carboxamide 3-20N-(4-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza- 501.27545α-androst-5-ene-17β-carboxamide 3-21N-(2-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α- 467.2469androst-5-ene-17β-carboxamide 3-22N-(4-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α- 467.2473androst-5-ene-17β-carboxamide 3-23N-(3-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α- 451.2755androst-5-ene-17β-carboxamide 3-24N-(4-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α- 451.2757androst-5-ene-17β-carboxamide 3-25N-(2-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α- 447.3012androst-5-ene-17β-carboxamide 3-26N-(3-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α- 447.3022androst-5-ene-17β-carboxamide 3-27N-(4-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α- 447.3016androst-5-ene-17β-carboxamide 3-28N-(1,1,1-trifluoroethyl)-3-oxo-4-cyclopropyl-4-aza-5α- 439.2559androst-5-ene-17β-carboxamide

EXAMPLE 4 Oral Composition

[1072] As a specific embodiment of an oral composition of a compound ofthis invention, 50 mg of a compound of the present invention isformatted with sufficient finely divided lactose to provide a totalamount of 580 to 590 mg to fill a size 0 hard gelatin capsule.

EXAMPLE 5

[1073] Transdermal Patch Formulation Ingredient Amount Compound offormula I 40 g Silicone fluid 45 g Colloidal silicone dioxide 2.5 g 

[1074] The silicone fluid and compound of structural formula I are mixedtogether and the colloidal silicone dioxide is added to increaseviscosity. The material is then dosed into a subsequently heat sealedpolymeric laminate comprised of the following: polyester release liner,skin contact adhesive composed of silicone or acrylic polymers, acontrol membrane which is a polyolefin (e.g. polyethylene, polyvinylacetate or polyurethane), and an impermeable backing membrane made of apolyester multilaminate. The resulting laminated sheet is then cut into10 cm² patches. For 100 Patches.

EXAMPLE 6

[1075] Suppository Ingredient Amount Compound of structural formula I 25 g Polyethylene glycol 1000 1481 g Polyethylene glycol 4000  494 g

[1076] The polyethylene glycol 1000 and polyethylene glycol 4000 aremixed and melted. The compound of structural formula I is mixed into themolten mixture, poured into molds and allowed to cool. For 1000suppositories.

EXAMPLE 7

[1077] Injectable solution Ingredient Amount compound of structuralformula I  5 g Buffering agents q.s. Propylene glycol 400 mg Water forinjection 600 mL

[1078] The compound of structural formula I and buffering agents aredissolved in the propylene glycol at about 50° C. The water forinjection is then added with stirring and the resulting solution isfiltered, filled into ampules, sealed and sterilized by autoclaving. For1000 Ampules.

EXAMPLE 8

[1079] Injectable solution Ingredient Amount Compound of structuralformula I  5 g Buffering agents q.s. Magnesium sulfate heptahydrate 100mg Water for injection 880 mL

[1080] The compound of structural formula I, magnesium sulfateheptahydrate and buffering agents are dissolved in the water forinjection with stirring, and the resulting solution is filtered, filledinto ampules, sealed and sterilized by autoclaving. For 1000 Ampules.

[1081] Following are assays to characterize the activity of the tissueselective androgen receptor modulators of the present invention.

In Vitro and In Vivo Assays FOR Identification of Compounds with SARMActivity Hydroxylapatite-based Radioligand Displacement Assay ofCompound Affinity for Endogenously Expressed AR Materials

[1082] Binding Buffer: TEGM (10 mM Tris-HCl, 1 mM EDTA, 10% glycerol, 1mM beta-mecaptoethanol, 10 mM Sodium Molybdate, pH 7.2) 50% HAP Slurry:Calbiochem Hydroxylapatite, Fast Flow, in 10 mM Tris, pH 8.0 and 1 mMEDTA.

[1083] Wash Buffer: 40 mM Tris, pH7.5, 100 mM KCl, 1 mM EDTA and 1 mMEGTA. 95% EtOH

[1084] Methyltrienolone, [17a-methyl-³H], (R1881*); NEN NET590Methyltrienolone (R1881), NEN NLP005 (dissolve in 95% EtOH)Dihydrotestosterone (DHT) [1,2,4,5,6,7-³H(N)] NEN NET453 HydroxylapatiteFast Flow; Calbiochem Cat#391947 Molybdate=Molybdic Acid (Sigma, M1651)

MDA-MB-453 Cell Culture Media

[1085] RPMI 1640 (Gibco 11835-055) w/23.8 mM NaHCO₃, 2 mM L-glutamine In500 mL of complete media Final conc. 10 mL (1M Hepes) 20 mM 5 mL (200 mML-glu)  4 mM 0.5 mL (10 mg/mL human insulin) 10 μg/mL in 0.01 N HClCalbiochem #407694-S) 50 mL FBS (Sigma F2442) 10% 1 mL (10 mg/mLGentamicin 20 μg/mL Gibco #15710-072)

Cell Passaging

[1086] Cells (Hall R. E., et al., European Journal of Cancer, Vol. 30A(4), 484-490 (1994)).are rinsed twice in PBS, phenol red freeTrypsin-EDTA is diluted in the same PBS 1:10 . The cell layers arerinsed with 1×Trypsin, extra Trypsin is poured out, and the cell layersare incubated at 37° C. for ˜2 min. The flask is tapped and checked tofor signs of cell detachment. Once the cells are starting to sliding offthe flask, the complete media is added to kill the trypsin. The cellsare counted at this point, then diluted to the appropriate concentrationand split into flasks or dishes for further culturing (Usually 1:3 to1:6 dilution).

Preparation of MDA-MB-453 Cell Lysate

[1087] When the MDA cells are 70 to 85% confluent, they are detached asdescribed above, and collected by centrifuging at 1000 g for 10 min at4° C. The cell pellet is washed 2×with TEGM (10 mM Tris-HCl, 1 mM EDTA,10% glycerol, 1 mM beta-mercaptoethanol, 10 mM Sodium Molybdate, pH7.2). After the final wash, the cells are resuspended in TEGM at aconcentration of 10⁷ cells/mL. The cell suspension is snap frozen inliquid N₂ or ethanol dry ice bath and transferred to −80° C. freezer ondry ice. Before setting up the binding assay, the frozen samples areleft on ice-water to just thaw (˜1 hr). Then the samples are centrifugedat 12,500 g to 20,000 g for 30 min at 4° C. The supernatant is used toset-up assay right away. If using 50 μL of supernatant, the testcompound can be prepared in 50 μL of the TEGM buffer.

Procedure for Multiple Compound Screening

[1088] 1×TEGM buffer is prepared, and the isotope-containing assaymixture is prepared in the following order: EtOH (2% final Conc. inreaction), ³H-R1881 or ³H-DHT (0.5 nM final Conc. in reaction) and1×TEGM. [e.g. For 100 samples, 200 μL (100×2) of EtOH+4.25 μL of 1:10³H-R1881 stock+2300 μL (100×23) 1×TEGM]. The compound is seriallydiluted, e.g., if starting final conc. is 1 μM, and the compound is in25 μL of solution, for duplicate samples, 75 μL of 4×1 μM solution ismade and 3 μL of 100 μM is added to 72 μL of buffer, and 1:5 serialdilution.

[1089] 25μL of ³H-R1881 trace and 25 μL compound solution are firstmixed together, followed by addition of 50 μL receptor solution. Thereaction is gently mixed, spun briefly at about 200 rpm and incubated at4° C. overnight. 100μL of 50% HAP slurry is prepared and 100 μL of 50%HAP slurry is added to the incubated reaction which is then vortexed andincubated on ice for 5 to 10 minutes. The reaction mixture is vortexedtwice more to resuspend HAP while incubating reaction. The samples in96-well format are then washed in wash buffer using The FilterMate™Universal Harvester plate washer (Packard). The washing processtransfers HAP pellet containing ligand-bound expressed receptor toUnifilter-96 GF/B filter plate (Packard). The HAP pellet on the filterplate is incubated with 50 μL of MICROSCINT (Packard) scintillint for ½hour before being counted on the TopCount micro scintillation counter(Packard). IC₅₀s are calculated using R1881 as a reference. Tissueselective androgen receptor modulators of the present inventiontypically have IC₅₀ values of 1 micromolar or less.

MMP1 Promoter Suppression, Transient Transfection Assay (TRAMPS)

[1090] HepG2 cells are cultured in phenol red free MEM containing 10 %charcoal-treated FCS at 37C with 5% CO₂. For transfection, cells areplated at 10,000 cells/well in 96 well white, clear bottom plates.Twenty four hours later, cells are co-transfected with a MMP1promoter-luciferase reporter construct and a rhesus monkey expressionconstruct (50: 1 ratio) using FuGENE6 transfection reagent, followingthe protocol recommended by manufacture. The MMP1 promoter-luciferasereporter construct is generated by insertion of a human MMP1 promoterfragment (−179/+63) into pGL2 luciferase reporter construct (Promega)and a rhesus monkey AR expression construct is generated in a CMV-Tag2Bexpression vector (Stratagene). Cells are further cultured for 24 hoursand then treated with ligands in the presence of 100 nMphorbol-12-myristate-13-acetate (PMA), used to increase the basalactivity of MMP1 promoter. The ligands are added at this point, at arange of 1000 nM to 0.03nM, 10 dilutions, at a concentration on 10×,1/10th volume. (example: 10 microliters of ligand at 10×added to 100microliters of media already in the well.) Cells are further culturedfor additional 48 hours. Cells are then washed twice with PBS and lysedby adding 70 μL of Lysis Buffer (1×, Promega) to the wells. Theluciferase activity is measured in a 96 well format using a 1450Microbeta Jet (Perkin Elmer) luminometer. AR agonism of tissue selectiveandrogen receptor modulators is presented as suppression of luciferasesignal from the PMA-stimulated control levels EC₅₀ and Emax values arereported. Tissue selective androgen receptor modulators of the presentinvention typically agonize repression typically with submicromolar EC₅₀values and Emax values greater than about 50%.

References

[1091] 1. Newberry E P, Willis D, Latifi T, Boudreaux J M, Towler D A.Fibroblast growth factor receptor signaling activates the humaninterstitial collagenase promoter via the bipartite Ets-API element. MolEndocrinol. 1997 Jul;11(8):1,129-44.

[1092] 2. Schneikert J, Peterziel H, Defossez P A, Klocker H, Launoit Y,Cato A C. Androgen receptor-Ets protein interaction is a novel mechanismfor steroid hormone-mediated down-modulation of matrix metalloproteinaseexpression. J Biol Chem. 1996 Sep 27;271(39):23907-13.

A Mammalian Two-Hybrid Assay for the Ligand-induced Interaction ofN-Terminus and C-Terminus Domains of the Androgen Receptor (AgonistMode)

[1093] This assay assesses the ability of AR agonists to induce theinteraction between the N-terminal domain (NTD) and C-terminal domain(CTD) of rhAR that reflects the in vivo virilizing potential mediated byactivated androgen receptors. (ref. 1). The interaction of NTD and CTDof rhAR is quantified as ligand induced association between aGal4DBD-rhARCTD fusion protein and a VP16-rhARNTD fusion protein asa-mammalian two-hybrid assay in CV-1 monkey kidney cells.

[1094] The day before transfection,•CV-1 cells are trypsinized andcounted, and then plated at 20,000 cells/well in 96 well plates orlarger plates (scaled up accordingly) in DMBM+10% FCS. The next morning,CV-1 cells are cotransfected with pCBB 1 (Gal4DBD-rhARLBD fusionconstruct expressed under the SV40 early promoter), pCBB₂ (VP16-rhAR NTDfusion construct expressed under the SV40 early promoter) and pFR (Gal4responsive luciferase reporter, Promega) using LIPOFECTAMINE PLUSreagent (GIBCO-BRL) following the procedure recommended by the vendor.Briefly, DNA admixture of 0.05 μg pCBB_(1, 0.05) μg pCBB2 and 0.1 ug ofpFR is mixed in 3.4 uL OPTI-MEM (GIBCO-BRL) is mixed with “PLUS Reagent”(1.6 μL, GIBCO-BRL) and incubated at room temperature (RT) for 15 min toform the pre-complexed DNA.

[1095] For each well, 0.4 μL LIPOFECTAMINE Reagent (GIBCO-BRL) isdiluted into 4.6 ,μL OPTI-MEM in a second tube and mixed to form thediluted LIPOFECTAMINE Reagent. The pre-complexed DNA (above) and thediluted LIPOFECTAMINE Reagent (above) are combined, mixed and incubatedfor 15 min at RT. The medium on the cells is replaced with 40 μL /wellOPTI-MEM, and 10 μL DNA-lipid complexes are added to each well. Thecomplexes are mixed into the medium gently and incubate at 37° C. at 5%CO₂ for 5 h. Following incubation, 200 μL /well D-MEM and 13%charcoal-stripped FCS is added, followed by incubation at 37° C. at 5%CO₂

[1096] After 24 hours, the test compounds are added at the desiredconcentration(s) (1 nM -10 μM). Forty eight hours later, luciferaseactivity is measured using LUC-Screen system (TROPIX) following themanufacture's protocol. The assay is conducted directly in the wells bysequential addition of 50 μL each of assay solution 1 followed by assaysolution 2. After incubation for 40 minutes ar room temperature,luminescence is directly measured with 2-5 second integration.

[1097] Activity of test compounds is calculated as the Emax relative tothe activity obtained by 3nM R1881. Typical tissue selective androgenreceptor modulators of the present invention display weak or no agonistactivity in this assay with less than 50% agonist activity at 10micromolar.

Reference

[1098] 1. He B, Kemppainen J A, Voegel J J, Gronemeyer H, Wilson E MActivation function In the human androgen receptor ligand binding domainmediates inter-domain communication with the NH(2)-terminal domain. JBiol Chem. V274: pp 37219-25, 1999.

A Mammalian Two-Hybrid Assay For Inhibition of Interaction betweenN-Terminus and C-Terminus Domains of Androgen Receptor (Antagonist Mode)

[1099] The assay assesses the ability of test compounds to antagonizethe stimulatory effects of R1881 on the interaction between NTD and CTDof rhAR in a mammalian two-hybrid assay in CV-1 cells as describedabove.

[1100] Forty eight hours after transfection, CV-1 cells are treated withtest compounds, typically at 10 μM, 3.3 μM, 1 μM, 0.33 μM, 100 nM, 33nM, 10 nM, 3.3 nM and 1 nM final concentrations. After incubation at a37° C. at 5% CO₂ for 10-30 minutes, an AR agonist methyltrienolone(R1881) is added to a final concentration of 0.3 nM and incubated at 37°C. Forty-eight hours later, luciferase activity is measured usingLUC-Screen system (TROPIX) following the protocol recommended by themanufacture. The ability of test compounds to antagonize the action ofR1881 is calculated as the relative luminescence compared to the valuewith 0.3 nM R1881 alone.

[1101] SARM compounds of the present invention typically displayantagonist activity in the present assay and have IC₅₀ values less than1 micromolar.

In Vivo Prostate Assay

[1102] Male Sprague-Dawley rats aged 9-10 weeks, the earliest age ofsexual maturity, are used in prevention mode. The goal is to measure thedegree to which androgen-like compounds delay the rapid deterioration(˜−85%) of the ventral prostate gland and seminal vesicles that occursduring a seven day period after removal of the testes (orchidectomy[ORX]).

[1103] Rats are orchidectomized (ORX). Each rat is weighed, thenanesthetized by isoflurane gas that is maintained to effect. A 1.5 cmanteroposterior incision is made in the scrotum. The right testicle isexteriorized. The spermatic artery and vas deferens is ligated with 4.0silk 0.5cm proximal to the testicle. The testicle is freed by one cut ofa small surgical scissors distal to the ligation site. The tissue stumpis returned to the scrotum. The same is repeated for the left testicle.When both stumps are returned to the scrotum, the scrotum and overlyingskin are sutured closed with 4.0 silk. For Sham-ORX, all proceduresexcepting ligation and scissors cutting are completed. The rats fullyrecover consciousness and full mobility within 10-15 minutes.

[1104] A dose of test compound is administered subcutaneously or orallyto the rat immediately after the surgical incision is sutured. Treatmentcontinues for an additional six consecutive days.

Necropsy and Endpoints

[1105] The rat is first weighed, then anesthetized in a CO₂ chamberuntil near death. Approximately 5 ml whole blood is obtained by cardiacpuncture. The rat is then examined for certain signs of death andcompleteness of ORX. Next, the ventral portion of the prostate gland islocated and blunt dissected free in a highly stylized fashion. Theventral prostate is blotted dry for 3-5 seconds and then weighed (VPW).Finally, the seminal vesicle is located and dissected free. The ventralseminal vesicle is blotted dry for 3-5 seconds and then weighed (SVWT).

[1106] Primary data for this assay are the weights of the ventralprostate and seminal vesicle. Secondary data include serum LH(luteinizing hormone and FSH (follicle stimulating hormone), andpossible serum markers of bone formation and virilization. Data areanalyzed by ANOVA plus Fisher PLSD post-hoc test to identify intergroupdifferences. The extent to which test compounds inhibit ORX-induced lossof VPW and SVWT is assessed.

In Vivo Bone Formation Assay

[1107] Female Sprague-Dawley rats aged 7-10 months are used in treatmentmode to simulate adult human females. The rats have been ovariectomized(OVX) 75-180 days previously, to cause bone loss and simulate estrogendeficient, osteopenic adult human females. Pre-treatment with a low doseof a powerful anti-resorptive, alendronate (0.0028 mpk SC, 2×/wk) isbegun on Day 0. On Day 15, treatment with test compound is started. Testcompound treatment occurs on Days 15-31 with necropsy on Day 32. Thegoal is to measure the extent to which androgen-like compounds increasethe amount of bone formation, shown by increased fluorochrome labeling,at the periosteal surface.

[1108] In a typical assay, nine groups of seven rats each are studied.

[1109] On Days 19 and 29 (fifth and fifteenth days of treatment), asingle subcutaneous injection of calcein (8mg/kg) is given to each rat.Necropsy and Endpoints

[1110] The rat is first weighed, then anesthetized in a CO₂ chamberuntil near death. Approximately 5 mL whole blood is obtained by cardiacpuncture. The rat is then examined for certain signs of deathand-completeness of OVX. First, the uterus is located, blunt dissectedfree in a highly stylized fashion, blotted dry for 3-5 seconds and thenweighed (UW). The uterus is placed in 10% neutral-buffered formalin.Next, the right leg is disarticulated at the hip. The femur and tibiaare separated at the knee, substantially defleshed, and then placed in70% ethanol.

[1111] A 1 cm segment of the central right femur, with the femoralproximal-distal midpoint ats center, is placed in a scintillation vialand dehydrated and defatted in graded alcohols and acetone, thenintroduced to solutions with increasing concentrations of methylmethacrylate. It is embedded in a mixture of 90% methyl methacrylate:10% dibutyl phthalate, that is allowed to polymerize over a 48-72hrperiod. The bottle is cracked and the plastic block is trimmed into ashape that conveniently fits the vice-like specimen holder of a Leica1600 Saw Microtome, with the long axis of the bone prepared forcross-sectioning. Three cross-sections of 85 μm thickness are preparedand mounted on glass slides. One section from each rat that approximatesthe midpoint of the bone is selected and blind-coded. The periostealsurface of each section is assessed for total periosteal surface, singlefluorochrome label, double fluorochrome label, and interlabel distance.

[1112] Primary data for this assay are the percentage of periostealsurface bearing double label and the mineral apposition rate (interlabeldistance(μm)/10d), semi-independent markers of bone formation. Secondarydata include uterus weight and histologic features. Tertiary endpointsmay include serum markers of bone formation and virilization. Data areanalyzed by ANOVA plus Fisher PLSD post-hoc test to identify intergroupdifferences. The extent to which test compounds increase bone formationendpoint will be assessed.

[1113] While the foregoing specification teaches the principles of thepresent invention, with examples provided for the purpose ofillustration, it will be understood that the practice of the inventionencompasses all of the usual variations, adoptions, or modifications, ascome within the scope of the following claims and their equivalents.

What is claimed is:
 1. A method for modulating the androgen receptor ina tissue selective manner in a patient in need of such modulationcomprising administering a therapeutically effective amount of acompound of structural formula I:

wherein: “a” and “b” are independently selected from a single bond and adouble bond; R¹is selected from: (1) C₁₋₃ alkyl, (2) C₂₋₃ alkenyl, (3)C₃₋₆ cycloalkyl, (4) C₁₋₃ alkyl wherein one or more of the hydrogenatoms has been replaced with a fluorine atom, (5) aryl, and (6)aryl-C₁₋₃ alkyl; R² is selected from: (1) aryl, either unsubstituted orsubstituted with one to three substituents selected from: (a) halogen,(b) aryl, (c) C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈cycloheteroalkyl, (f) aryl C₁-₆alkyl, (g) amino C₀₋₆alkyl, (h) C₁₋₆alkylamino C₀₋₆alkyl, (i) (C₀₋₆alkyl)2amino C₀₋₆alkyl, (j) aryl C₀₋₆alkylamino C₀₋₆alkyl, (k) (aryl C₀₋₆ alkyl)2amino C₀₋₆alkyl, (l) C₁₋₆alkylthio, (m) aryl C₀₋₆alkylthio, (n) C₁₋₆ alkylsulfinyl, (o) arylC₀₋₆alkylsulfinyl, (p) C₁₋₆ alkylsulfonyl, (q) aryl C₀₋₆alkylsulfonyl,(r) C₁₋₆ alkoxy C₀₋₆alkyl, (s) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (t)hydroxycarbonyl C₀₋₆alkyl, (u) C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (v) arylC₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonyl C₁₋₆ alkyloxy, (x)hydroxy C₀₋₆alkyl, (y) cyano, (z) nitro, (aa) perfluoroC₁₋₄alkyl, (bb)perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆ alkylcarbonyloxy, (ee) arylC₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆ carbonylamino, (gg) aryl C₀₋₆alkylcarbonylamino, (hh) C₁₋₆ alkylsulfonylamino, (ii) arylC₀₋₆alkylsulfonylamino, (jj) C₁₋₆ alkoxycarbonylamino, (kk) aryl C₀₋₆alkoxycarbonylamino, (ll) C1-6alkylaminocarbonylamino, (mm)arylC₀₋₆alkylaminocarbonylamino, (nn) (C₁₋₆alkyl)₂ aminocarbonylamino, (oo)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (pp) (C₁₆alkyl)₂ aminocarbonyloxy,(qq) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, (rr) C₀₋₆alkylcarbonylC₀₋₆alkyl, and (ss) aryl C₀₋₆alkylcarbonyl C₀₋₆alkyl; (2) C₁₋₈ alkyl,unsubstituted or substituted with one to three substituentsindependently selected from: (a) halogen, (b) aryl, (c) C₁₋₈ alkyl, (d)C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) amino, (g) C₁₋₆alkylamino, (h) (C₁₋₆ alkyl)₂amino, (i) aryl C₀₋₆ alkylamino, (j) (arylC₀₋₆ alkyl)₂amino, (k) C₁₋₆ alkylthio, (l) aryl C₀₋₆alkylthio, (m) C₁₋₆alkylsulfinyl, (n) aryl C₀₋₆alkylsulfinyl, (o) C₁₋₆ alkylsulfonyl, (p)aryl C₀₋₆alkylsulfonyl, (q) C₁₋₆ alkoxy, (r) aryl C₀₋₆ alkoxy, (s)hydroxycarbonyl, (t) C₁₋₆ alkoxycarbonyl, (u) aryl C₀₋₆ alkoxycarbonyl,(v) hydroxycarbonyl C₀₋₆ alkyloxy, (w) hydroxy, (x) cyano, (y) nitro,(z) perfluoroC₁₋₄alkyl, (aa) perfluoroC1-4alkoxy, (bb) oxo, (cc) C₁₋₆alkylcarbonyloxy, (dd) aryl C₀₋₆alkylcarbonyloxy, (ee) alkyl C₁₋₆carbonylamino, (ff) aryl C₀₋₆ alkylcarbonylamino, (gg) C₁₋₆alkylsulfonylamino, (hh) aryl C₀₋₆alkylsulfonylamino, (ii) C₁₋₆alkoxycarbonylamino, (j) aryl C₀₋₆ alkoxycarbonylamino, (kk)C₁₋₆alkylaminocarbonylamino, (ll) aryl C₀₋₆alkylaminocarbonylamino, (mm)(C₁₋₆alkyl)₂ aminocarbonylamino, (nn) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy, (pp) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (qq) spiro-C₃-8cycloalkyl; (3)perfluoroC₁₋₈ alkyl, (4) C₂₋₈ alkenyl, unsubstituted or substituted withone to three substituents independently selected from: (a) halogen, (b)aryl, (c) C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl,(f) amino, (g) C₁₋₆ alkylamino, (h) (C₀₋₆alkyl)₂amino, (i) aryl C₀₋₆alkylamino, (j) (aryl C₀₋₆ alkyl)₂amino, (k) C₁₋₆ alkylthio, (l) arylC₀₋₆alkylthio, (m) C₁₋₆ alkylsulfinyl, (n) aryl C₀₋₆alkylsulfinyl, (o)C₁₋₆ alkylsulfonyl, (p) aryl C₀₋₆alkylsulfonyl, (q) C₁₋₆ alkoxy, (r)aryl C₀₋₆ alkoxy, (s) hydroxycarbonyl, (t) C₁₋₆ alkoxycarbonyl, (u) arylC₀₋₆ alkoxycarbonyl, (v) hydroxycarbonyl C₁₋₆ alkyloxy, (w) hydroxy, (x)cyano, (y) nitro, (z) perfluoroC₁₋₄alkyl, (aa) perfluoroC₁₋₄alkoxy, (bb)oxo, (cc) C₁₋₆ alkylcarbonyloxy, (dd) aryl C₀₋₆alkylcarbonyloxy, (ee)alkyl C₁₋₆ carbonylamino, (ff) aryl C₀₋₆ alkylcarbonylamino, (gg) C₁₋₆alkylsulfonylamino, (hh) aryl C₀₋₆alkylsulfonylamino, (ii) C₁₋₆alkoxycarbonylamino, (j) aryl C₀₋₆ alkoxycarbonylamino, (kk)C₁₋₆alkylaminocarbonylamino, (ll) aryl C₀₋₆alkylaminocarbonylamino, (mm)(C₁₋₆alkyl)₂ aminocarbonylamino, (nn) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy, (pp) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (qq) spiro-C₃₋₈cycloalkyl;. (5) C₃₋₈cycloalkyl, either unsubstituted or substituted with one to 3substituents selected from: (a) halogen, (b) aryl, (c) C₁₋₈ alkyl, (d)C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) aryl C₀₋₆alkyl, (g)amino C₀₋₆alkyl, (h) C₁₋₆ alkylamino C₀₋₆alkyl, (i) (C₁₋₆ alkyl)₂aminoC₀₋₆alkyl, (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (k) (aryl C₀₋₆alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆ alkylthio, (m) aryl C₀₋₆alkylthio, (n)C₁₋₆ alkylsulfinyl, (o) aryl C₀₋₆alkylsulfinyl, (p) C₀₋₆alkylsulfonyl,(q) aryl C₀₋₆alkylsulfonyl, (r) C₁₋₆ alkoxy C₀₋₆alkyl, (s) aryl C₀₋₆alkoxy C₀₋₆alkyl, (t) hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonylC₀₋₆alkyl, (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonylC₁₋₆ alkyloxy, (x) hydroxy C₀₋₆alkyl, (y) cyano, (z) nitro, (aa)perfluoroC₁₋₄alkyl, (bb) perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆alkylcarbonyloxy, (ee) aryl C₀₋₆alkylcarbonyloxy, (ff) alkylC₀₋₆carbonylamino, (gg) aryl C₀₋ ₆ alkylcarbonylamino, (hh)C₀₋₆alkylsulfonylamino, (ii) aryl C₀₋₆alkylsulfonylamino, (jj) C₁₋₆alkoxycarbonylamino, (kk) aryl C₀₋₆ alkoxycarbonylamino, (ll)C₁₋₆alkylaminocarbonylamino, (mm) aryl C₀₋₆alkylaminocarbonylamino, (nn)(C₁₋₆alkyl)₂ aminocarbonylamino, (oo) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (pp) (C₁₋₆alkyl)₂ aminocarbonyloxy, (qq) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, (rr) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and (ss)spiro-C₃₋₈cycloalkyl; (6) cycloheteroalkyl, unsubstituted or substitutedwith one to three substituents selected from: (a) halogen, (b) aryl, (c)C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) arylC₀₋₆alkyl, (g) amino C₀₋₆alkyl, (h) C₀₋₆alkylamino C₀₋₆alkyl, (i) (C₁₋₆alkyl)₂amino C₀₋₆alkyl, (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (k) (arylC₀₋₆ alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆ alkylthio, (m) aryl C₀₋₆alkylthio,(n) C₁₋₆ alkylsulfinyl, (o) aryl C₀₋₆ alkylsulfinyl, (p)C₀₋₆alkylsulfonyl, (q) aryl C₀₋₆alkylsulfonyl, (r) C₁₋₆ alkoxyC₀₋₆alkyl, (s) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (t) hydroxycarbonylC₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (v) aryl C₀₋₆alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonyl C₁₋₆ alkyloxy, (x) hydroxyC₀₋₆alkyl, (y) cyano, (z) nitro, (aa) perfluoroC₁₋₄alkyl, (bb)perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆ alkylcarbonyloxy, (ee) arylC₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆ carbonylamino, (gg) aryl C₀₋₆alkylcarbonylamino, (hh) C₀₋₆ alkylsulfonylamino, (ii) arylC₀₋₆alkylsulfonylamino, (j) C₁₋₆ alkoxycarbonylamino, (kk) aryl C₀₋₆alkoxycarbonylamino, (ll) C1-6alkylaminocarbonylamino, (mm)arylC₀₋₆alkylaminocarbonylamino, (nn) (C₁₋₆alkyl)₂ aminocarbonylamino, (oo)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (pp) (C16alkyl)₂ aminocarbonyloxy,(qq) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, and (rr) C₀₋₆alkylcarbonylC₀₋₆alkyl, and (ss) spiro C₃₋₈cycloalkyl, provided that any heteroatomsubstituent is bonded to a carbon atom in the cycloheteroalkyl ring; R³is selected from H and C₁₋₈ alkyl, or R² and R³, together with thenitrogen atom to which they are attached, form a 5- to 7-memberedheterocyclic ring, optionally containing one or two additionalheteroatoms selected from N, S, and O, optionally having one or moredegrees of unsaturation, optionally fused to a 6-membered heteroaromaticor aromatic ring, either unsubstituted or substituted with one to threesubstituents selected from: (1) halogen, (2) aryl, (3) C₁₋₈ alkyl, (4)C₃₋₈ cycloalkyl, (5) C₃₋₈ cycloheteroalkyl, (6) aryl C₁₋₆alkyl, (7)amino C₀₋₆alkyl, (8) C₁₋₆ alkylamino C₀₋₆alkyl, (9) (C₁₋₆ alkyl)₂aminoC₀₋₆alkyl, (10) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (11) (aryl C₀₋₆alkyl)₂amino C₀₋₆alkyl, (12) C₁₋₆ alkylthio, (13) aryl C₀₋₆alkylthio,(14) C₁₋₆ alkylsulfinyl, (15) aryl C₀₋₆alkylsulfinyl, (16) C₁₋₆alkylsulfonyl, (17) aryl C₀₋₆alkylsulfonyl, (18) C₁₋₆ alkoxy C₀₋₆alkyl,(19) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (20) hydroxycarbonyl C₀₋₆alkyl, (21)C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (22) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl,(23) hydroxycarbonyl C₁₋₆ alkyloxy, (24) hydroxy C₀₋₆alkyl, (25) cyano,(26) nitro, (27) perfluoroC₁₋₄alkyl, (28) perfluoroC₁₋₄alkoxy, (29) oxo,(30) C₁₋₆ alkylcarbonyloxy, (31) aryl C₀₋₆alkylcarbonyloxy, (32) C₁₋₆alkyl carbonylamino, (33) aryl C₀₋₆ alkylcarbonylamino, (34) C₀₋₆alkylsulfonylamino, (35) aryl C₀₋₆alkylsulfonylamino, (36) C₁₋₆alkoxycarbonylamino, (37) aryl C₀₋₆ alkoxycarbonylamino, (38)C₁₋₆alkylaminocarbonylamino, (39) aryl C₀₋₆alkylaminocarbonylamino, (40)(C6alkyl)₂ aminocarbonylamino, (41) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (42) (C_(b 1-6)alkyl)₂ aminocarbonyloxy, (43) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (44) spiro-C₃₋₈cycloalkyl providedthat any heteroatom substituent is bonded to a carbon atom in theheterocyclic ring; R⁴ and R⁵ are each independently selected from (1)hydrogen, (2) halogen, (3) aryl, (4) C₁₋₈ alkyl, (5) C₃₋₈ cycloalkyl,(6) C₃₋₈ cycloheteroalkyl, (7) aryl C₁₋₆alkyl, (8) amino C₀₋₆alkyl, (9)C₁₋₆ alkylamino C₀₋₆alkyl, (10) (C₀₋₆alkyl)₂amino C₀₋₆alkyl, (11) arylC₀₋₆ alkylamino C₀₋₆alkyl, (12) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (13)C₁₋₆ alkylthio, (14) aryl C₀₋₆alkylthio, (15) C₁₋₆ alkylsulfinyl, (16)aryl C₀₋₆alkylsulfinyl, (17) C₁₋₆ alkylsulfonyl, (18) arylC₀₋₆alkylsulfonyl, (19) C₁₋₆ alkoxy C₀₋₆alkyl, (20) aryl C₀₋₆ alkoxyC₀₋₆alkyl, (21) hydroxycarbonyl C₀₋₆alkyl, (22) C₁₋₆ alkoxycarbonylC₀₋₆alkyl, (23) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (24) hydroxycarbonylC₁₋₆ alkyloxy, (25) hydroxy C₀₋₆alkyl, (26) cyano, (27) nitro, (28)perfluoroC₁₋₄alkyl, (29) perfluoroC₁₋₄alkoxy, (30) C₀₋₆alkylcarbonylC₀₋₆alkyl, (31) C₁₋₆ alkylcarbonyloxy, (32) aryl C₀₋₆alkylcarbonyloxy,(33) C₁₋₆ alkyl carbonylamino, (34) aryl C₀₋₆ alkylcarbonylamino, (35)C₁₋₆ alkylsulfonylamino, (36) aryl C₀₋₆alkylsulfonylamino, (37) C₁₋₆alkoxycarbonylamino, (38) aryl C₀₋₆ alkoxycarbonylamino, (39)C₁₋₆alkylaminocarbonylamino, (40) aryl C₀₋₆alkylaminocarbonylamino, (41)(C₁₋₆alkyl)₂ aminocarbonylamino, (42) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (43) (C₁₋₆alkyl)₂ aminocarbonyloxy, and (44) (arylC₀₋₆alkyl)₂ aminocarbonyloxy; or, R⁴ and R⁵ together form an oxo groupor ═CH—R⁶ or a spiro C₃₋₇ cycloalkyl ring, unsubstituted or substitutedwith R⁶; R⁶ is selected from: (1) hydrogen, and (2) C₁₋₄ alkyl; or apharmaceutically acceptable salt thereof. cm
 2. A method of agonizingthe androgen receptor comprising administering to a patient atherapeutically effective amount of a compound of structural formula I:

wherein: “a” and “b” are independently selected from a single bond and adouble bond; R¹ is selected from: (1) C₁₋₃ alkyl, (2) C₂₋₃ alkenyl, (3)C₃₋₆ cycloalkyl, (4) C₁₋₃ alkyl wherein one or more of the hydrogenatoms has been replaced with a fluorine atom, (5) aryl, and (6)aryl-C₁₋₃ alkyl; R² is selected from: (1) aryl, either unsubstituted orsubstituted with one to three substituents selected from: (a) halogen,(b) aryl, (c) C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈cycloheteroalkyl, (f) aryl C₁₋₆alkyl, (g) amino C₀₋₆alkyl, (h) C₁₋₆alkylamino C₀₋₆alkyl, (i) (C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (j) aryl C₀₋₆alkylamino C₀₋₆alkyl, (k) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆alkylthio, (m) aryl C₀₋₆alkylthio, (n) C₁₋₆ alkylsulfinyl, (o) arylC₀₋₆alkylsulfinyl, (p) C₁₋₆ alkylsulfonyl, (q) aryl C₀₋₆alkylsulfonyl,(r) C₁₋₆ alkoxy C₀₋₆alkyl, (s) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (t)hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (v) arylC₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonyl C₁₋₆ alkyloxy, (x)hydroxy C₀₋₆alkyl, (y) cyano, (z) nitro, (aa) perfluoroC₁₋₄alkyl, (bb)perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆ alkylcarbonyloxy, (ee) arylC₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆ carbonylamino, (gg) aryl C₀₋₆alkylcarbonylamino, (hh) C₁₋₆ alkylsulfonylamino, (ii) arylC₀₋₆alkylsulfonylamino, (jj) C₁₋₆ alkoxycarbonylamino, (kk) aryl C₀₋₆alkoxycarbonylamino, (ll) C₁₋₆alkylaminocarbonylamino, (mm) arylC₀₋₆alkylaminocarbonylamino, (nn) (C₁₋₆alkyl)₂ aminocarbonylamino, (oo)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (pp) (C₁₋₆alkyl)₂aminocarbonyloxy, (qq) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, (rr)C₀₋₆alkylcarbonyl C₀₋₆alkyl, and (ss) aryl C₀₋₆alkylcarbonyl C₀₋₆alkyl;(2) C₁₋₈ alkyl, unsubstituted or substituted with one to threesubstituents independently selected from: (a) halogen, (b) aryl, (c)C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) amino,(g) C₁₋₆ alkylamino, (h) (C₁₋₆ alkyl)₂amino, (i) aryl C₀₋₆ alkylamino,(j) (aryl C₀₋₆ alkyl)₂amino, (k) C₁₋₆ alkylthio, (l) aryl C₀₋₆alkylthio,(m) C₁₋₆ alkylsulfinyl, (n) aryl C₀₋₆alkylsulfinyl, (o) C₁₋₆alkylsulfonyl, (p) aryl C₀₋₆alkylsulfonyl, (q) C₁₋₆ alkoxy, (r) arylC₀₋₆ alkoxy, (s) hydroxycarbonyl, (t) C₁₋₆ alkoxycarbonyl, (u) aryl C₀₋₆alkoxycarbonyl, (v) hydroxycarbonyl C₁₋₆ alkyloxy, (w) hydroxy, (x)cyano, (y) nitro, (z) perfluoroC₁₋₄alkyl, (aa) perfluoroC₁₋₄alkoxy, (bb)oxo, (cc) C₁₋₆ alkylcarbonyloxy, (dd) aryl C₀₋₆alkylcarbonyloxy, (ee)alkyl C₁₋₆ carbonylamino, (ff) aryl C₀₋₆ alkylcarbonylamino, (gg) C₁₋₆alkylsulfonylamino, (hh) aryl C₀₋₆alkylsulfonylamino, (ii) C₁₋₆alkoxycarbonylamino, (jj) aryl C₀₋₆ alkoxycarbonylamino, (kk)C₁₋₆alkylaminocarbonylamino, (ll) aryl C₀₋₆alkylaminocarbonylamino,(mm)(C₁₋₆alkyl)₂ aminocarbonylamino, (nn) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy, (pp) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (qq) spiro-C₃₋₈cycloalkyl; (3)perfluoroC₁₋₈ alkyl, (4) C₂₋₈ alkenyl, unsubstituted or substituted withone to three substituents independently selected from: (a) halogen, (b)aryl, (c) C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl,(f) amino, (g) C₁₋₆ alkylamino, (h) (C₁₋₆ alkyl)₂amino, (i) aryl C₀₋₆alkylamino, (j) (aryl C₀₋₆ alkyl)₂amino, (k) C₁₋₆ alkylthio, (l) arylC₀₋₆alkylthio, (m) C₁₋₆ alkylsulfinyl, (n) aryl C₀₋₆alkylsulfinyl, (o)C₁₋₆ alkylsulfonyl, (p) aryl C₀₋₆alkylsulfonyl, (q) C₁₋₆ alkoxy, (r)aryl C₀₋₆ alkoxy, (s) hydroxycarbonyl, (t) C₁₋₆ alkoxycarbonyl, (u) arylC₀₋₆ alkoxycarbonyl, (v) hydroxycarbonyl C₁₋₆ alkyloxy, (w) hydroxy, (x)cyano, (y) nitro, (z) perfluoroC₁₋₄alkyl, (aa) perfluoroC₁₋₄alkoxy, (bb)oxo, (cc) C₁₋₆ alkylcarbonyloxy, (dd) aryl C₀₋₆alkylcarbonyloxy, (ee)alkyl C₁₋₆ carbonylamino, (ff) aryl C₀₋₆ alkylcarbonylamino, (gg) C₁₋₆alkylsulfonylamino, (hh) aryl C₀₋₆alkylsulfonylamino, (ii) C₁₋₆alkoxycarbonylamino, (jj) aryl C₀₋₆ alkoxycarbonylamino, (kk)C₁₋₆alkylaminocarbonylamino, (ll) aryl C₀₋₆alkylaminocarbonylamino,(mm)(C₁₋₆alkyl)₂ aminocarbonylamino, (nn) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy, (pp) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (qq) spiro-C₃₋₈cycloalkyl; (5) C₃₋₈cycloalkyl, either unsubstituted or substituted with one to 3substituents selected from: (a) halogen, (b) aryl, (c) C₁₋₈ alkyl, (d)C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) aryl C₁₋₆alkyl, (g)amino C₀₋₆alkyl, (h) C₁₋₆ alkylamino C₀₋₆alkyl, (i) (C₁₋₆ alkyl)₂aminoC₀₋₆alkyl, (j) aryl C₀₋₆ alkylaminoC₀₋₆alkyl, (k) (aryl C₀₋₆alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆ alkylthio, (m) aryl C₀₋₆alkylthio, (n)C₁₋₆ alkylsulfinyl, (o) aryl C₀₋₆alkylsulfinyl, (p) C₁₋₆ alkylsulfonyl,(q) aryl C₀₋₆alkylsulfonyl, (r) C₁₋₆ alkoxy C₀₋₆alkyl, (s) aryl C₀₋₆alkoxy C₀₋₆alkyl, (t) hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonylC₀₋₆alykl, (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonylC₁₋₆ alkyloxy, (x) hydroxy C₀₋₆alkyl, (y) cyano, (z) nitro, (aa)perfluoroC₁₋₄alkyl, (bb) perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆alkylcarbonyloxy, (ee) aryl C₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆carbonylamino, (gg) aryl C₀₋₆ alkylcarbonylamino, (hh) C₁₋₆alkylsulfonylamino, (ii) aryl C₀₋₆alkylsulfonylamino, (jj) C₁₋₆alkoxycarbonylamino, (kk) aryl C₀₋₆ alkoxycarbonylamino, (ll)C₁₋₆alkylaminocarbonylamino, (mm) aryl C₀₋₆alkylaminocarbonylamino, (nn)(C₁₋₆alkyl)₂ aminocarbonyl amino, (oo) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (pp) (C₁₋₆alkyl)₂ aminocarbonyloxy, (qq) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, (rr) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and (ss)spiro-C₃₋₈cycloalkyl; (6) cycloheteroalkyl, unsubstituted or substitutedwith one to three substituents selected from: (a) halogen, (b) aryl, (c)C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) arylC₁₋₆alkyl, (g) amino C₀₋₆alkyl, (h) C₁₋₆ alkylamino C₀₋₆alkyl, (i) (C₁₋₆alkyl)₂amino C₀₋₆alkyl, (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (k) (arylC₀₋₆ alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆ alkylthio, (m) aryl C₀₋₆alkylthio,(n) C₁₋₆ alkylsulfinyl, (o) aryl C₀₋₆alkylsulfinyl, (p) C₁₋₆alkylsulfonyl, (q) aryl C₀₋₆alkylsulfonyl, (r) C₁₋₆ alkoxy C₀₋₆alkyl,(s) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (t) hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆alkoxycarbonyl C₀₋₆alkyl, (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w)hydroxycarbonyl C₁₋₆ alkyloxy, (x) hydroxy C₀₋₆alkyl, (y) cyano, (z)nitro, (aa) perfluoroC₁₋₄alkyl, (bb) perfluoroC₁₋₄alkoxy, (cc) oxo, (dd)C₁₋₆ alkylcarbonyloxy, (ee) aryl C₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆carbonylamino, (gg) aryl C₀₋₆ alkylcarbonylamino, (hh) C₁₋₆alkylsulfonylamino, (ii) aryl C₀₋₆alkylsulfonylamino, (jj) C₁₋₆alkoxycarbonylamino, (kk) aryl C₀₋₆ alkoxycarbonylamino, (ll)C₁₋₆alkylaminocarbonylamino, (mm) aryl C₀₋₆alkylaminocarbonylamino, (nn)(C₁₋₆alkyl)₂ aminocarbonylamino, (oo) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (pp) (C₁₋₆alkyl)₂ aminocarbonyloxy, (qq) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (rr) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and(ss) spiro C₃₋₈cycloalkyl provided that any heteroatom substituent isbonded to a carbon atom in the cycloheteroalkyl ring; R³ is selectedfrom H and C₁₋₈ alkyl, or R² and R³, together with the nitrogen atom towhich they are attached, form a 5- to 7-membered heterocyclic ring,optionally containing one or two additional heteroatoms selected from N,S, and O, optionally having one or more degrees of unsaturation,optionally fused to a 6-membered heteroaromatic or aromatic ring, eitherunsubstituted or substituted with one to three substituents selectedfrom: (1) halogen, (2) aryl, (3) C₁₋₈ alkyl, (4) C₃₋₈ cycloalkyl, (5)C₃₋₈ cycloheteroalkyl, (6) aryl C₁₋₆alkyl, (7) amino C₀₋₆alkyl, (8) C₁₋₆alkylamino C₀₋₆alkyl, (9) (C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (10) aryl C₀₋₆alkylamino C₀₋₆alkyl, (11) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (12) C₁₋₆alkylthio, (13) aryl C₀₋₆alkylthio, (14) C₁₋₆ alkylsulfinyl, (15) arylC₀₋₆alkylsulfinyl, (16) C₁₋₆ alkylsulfonyl, (17) aryl C₀₋₆alkylsulfonyl,(18) C₁₋₆ alkoxy C₀₋₆alkyl, (19) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (20)hydroxycarbonyl C₀₋₆alkyl, (21) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (22) arylC₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (23) hydroxycarbonyl C₁₋₆ alkyloxy, (24)hydroxy C₀₋₆alkyl, (25) cyano, (26) nitro, (27) perfluoroC₁₋₄alkyl, (28)perfluoroC₁₋₄alkoxy, (29) oxo, (30) C₁₋₆ alkylcarbonyloxy, (31) arylC₀₋₆alkylcarbonyloxy, (32) C₁₋₆ alkyl carbonylamino, (33) aryl C₀₋₆alkylcarbonylamino, (34) C₁₋₆ alkylsulfonylamino, (35) arylC₀₋₆alkylsulfonylamino, (36) C₁₋₆ alkoxycarbonylamino, (37) aryl C₀₋₆alkoxycarbonylamino, (38) C₁₋₆alkylaminocarbonylamino, (39) arylC₀₋₆alkylaminocarbonylamino, (40) (C₁₋₆alkyl)₂ aminocarbonylamino, (41)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (42) (C₁₋₆alkyl)₂aminocarbonyloxy, (43) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, and (44)spiro-C₃₋₈cycloalkyl provided that any heteroatom substituent is bondedto a carbon atom in the heterocyclic ring; R⁴ and R⁵ are eachindependently selected from (1) hydrogen, (2) halogen, (3) aryl, (4)C₁₋₈ alkyl, (5) C₃₋₈ cycloalkyl, (6) C₃₋₈ cycloheteroalkyl, (7) arylC₁₋₆alkyl, (8) amino C₀₋₆alkyl, (9) C₁₋₆ alkylamino C₀₋₆alkyl, (10)(C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (11) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (12)(aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (13) C₁₋₆ alkylthio, (14) arylC₀₋₆alkylthio, (15) C₁₋₆ alkylsulfinyl, (16) aryl C₀₋₆alkylsulfinyl,(17) C₁₋₆ alkylsulfonyl, (18) aryl C₀₋₆alkylsulfonyl, (19) C₁₋₆ alkoxyC₀₋₆alkyl, (20) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (21) hydroxycarbonylC₀₋₆alkyl, (22) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (23) aryl C₀₋₆alkoxycarbonyl C₀₋₆alkyl, (24) hydroxycarbonyl C₁₋₆ alkyloxy, (25)hydroxy C₀₋₆alkyl, (26) cyano, (27) nitro, (28) perfluoroC₁₋₄alkyl, (29)perfluoroC₁₋₄alkoxy, (30) C₀₋₆alkylcarbonyl C₀₋₆alkyl, (31) C₁₋₆alkylcarbonyloxy, (32) aryl C₀₋₆alkylcarbonyloxy, (33) C₁₋₆ alkylcarbonylamino, (34) aryl C₀₋₆ alkylcarbonylamino, (35) C₁₋₆alkylsulfonylamino, (36) aryl C₀₋₆alkylsulfonylamino, (37) C₁₋₆alkoxycarbonylamino, (38) aryl C₀₋₆ alkoxycarbonylamino, (39)C₁₋₆alkylaminocarbonylamino, (40) aryl C₀₋₆alkylaminocarbonylamino, (41)(C₁₋₆alkyl)₂ aminocarbonylamino, (42) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (43) (C₁₋₆alkyl)₂ aminocarbonyloxy, and (44) (arylC₀₋₆alkyl)₂ aminocarbonyloxy; or, R⁴ and R⁵ together form an oxo groupor ═CH—R⁶ or a Spiro C₃₋₇ cycloalkyl ring, unsubstituted or substitutedwith R⁶; R⁶ is selected from: (1) hydrogen, and (2) C₁₋₄ alkyl; or apharmaceutically acceptable salt thereof.
 3. The method according toclaim 1 wherein the androgen receptor is antagonized in the prostate ofa male patient or in the uterus of a female patient and agonized in boneor muscle tissue.
 4. A method of treating a condition which is caused byandrogen deficiency or which can be ameliorated by androgenadministration selected from: osteoporosis, periodontal disease, bonefracture, bone damage following bone reconstructive surgery, sarcopenia,frailty, aging skin, male hypogonadism, post-menopausal symptoms inwomen, atherosclerosis, hypercholesterolemia, hyperlipidemia, aplasticanemia and other hematopoietic disorders, pancreatic cancer, renalcancer, arthritis and joint repair, in a patient in need of suchtreatment, comprising administering a therapeutically effective amountof a compound of structural formula I:

wherein: “a” and “b” are independently selected from a single bond and adouble bond; R¹ is selected from: (1) C₁₋₃ alkyl, (2) C₂₋₃ alkenyl, (3)C₃₋₆ cycloalkyl, (4) C₁₋₃ alkyl wherein one or more of the hydrogenatoms has been replaced with a fluorine atom, (5) aryl, and (6)aryl-C₁₋₃ alkyl; R² is selected from: (1) aryl, either unsubstituted orsubstituted with one to three substituents selected from: (a) halogen,(b) aryl, (c) C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈cycloheteroalkyl, (f) aryl C₁₋₆alkyl, (g) amino C₀₋₆alkyl, (h) C₁₋₆alkylamino C₀₋₆alkyl, (i) (C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (j) aryl C₀₋₆alkylamino C₀₋₆alkyl, (k) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆alkylthio, (m) aryl C₀₋₆alkylthio, (n) C₁₋₆ alkylsulfinyl, (o) arylC₀₋₆alkylsulfinyl, (p) C₁₋₆ alkylsulfonyl, (q) aryl C₀₋₆alkylsulfonyl,(r) C₁₋₆ alkoxy C₀₋₆alkyl, (s) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (t)hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (v) arylC₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonyl C₁₋₆ alkyloxy, (x)hydroxy C₀₋₆alkyl, (y) cyano, (z) nitro, (aa) perfluoroC₁₋₄alkyl, (bb)perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆ alkylcarbonyloxy, (ee) arylC₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆ carbonylamino, (gg) aryl C₀₋₆alkylcarbonylamino, (hh) C₁₋₆ alkylsulfonylamino, (ii) arylC₀₋₆alkylsulfonylamino, (jj) C₁₋₆ alkoxycarbonylamino, (kk) aryl C₀₋₆alkoxycarbonylamino, (ll) C₁₋₆alkylaminocarbonylamino, (mm) arylC₀₋₆alkylaminocarbonylamino, (nn) (C₁₋₆alkyl)₂ aminocarbonylamino, (oo)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (pp) (C₁₋₆alkyl)₂aminocarbonyloxy, (qq) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, (rr)C₀₋₆alkylcarbonyl C₀₋₆alkyl, and (ss) aryl C₀₋₆alkylcarbonyl C₀₋₆alkyl;(2) C₁₋₈ alkyl, unsubstituted or substituted with one to threesubstituents independently selected from: (a) halogen, (b) aryl, (c)C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) amino,(g) C₁₋₆ alkylamino, (h) (C₁₋₆ alkyl)₂amino, (i) aryl C₀₋₆ alkylamino,(j) (aryl C₀₋₆ alkyl)₂amino, (k) C₁₋₆ alkylthio, (l) aryl C₀₋₆alkylthio,(m) C₁₋₆ alkylsulfinyl, (n) aryl C₀₋₆alkylsulfinyl, (o) C₁₋₆alkylsulfonyl, (p) aryl C₀₋₆alkylsulfonyl, (q) C₁₋₆ alkoxy, (r) arylC₀₋₆ alkoxy, (s) hydroxycarbonyl, (t) C₁₋₆ alkoxycarbonyl, (u) aryl C₀₋₆alkoxycarbonyl, (v) hydroxycarbonyl C₁₋₆ alkyloxy, (w) hydroxy, (x)cyano, (y) nitro, (z) perfluoroC₁₋₄alkyl, (aa) perfluoroC₁₋₄alkoxy, (bb)oxo, (cc) C₁₋₆ alkylcarbonyloxy, (dd) aryl C₀₋₆alkylcarbonyloxy, (ee)alkyl C₁₋₆ carbonylamino, (ff) aryl C₀₋₆ alkylcarbonylamino, (gg) C₁₋₆alkylsulfonylamino, (hh) aryl C₀₋₆alkylsulfonylamino, (ii) C₁₋₆alkoxycarbonylamino, (jj) aryl C₀₋₆ alkoxycarbonylamino, (kk)C₁₋₆alkylaminocarbonylamino, (ll) aryl C₀₋₆alkylaminocarbonylamino, (mm)(C₁₋₆alkyl)₂ aminocarbonylamino, (nn) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy, (pp) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (qq) spiro-C₃₋₈cycloalkyl; (3)perfluoroC₁₋₈ alkyl, (4) C₂₋₈ alkenyl, unsubstituted or substituted withone to three substituents independently selected from: (a) halogen, (b)aryl, (c) C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl,(f) amino, (g) C₁₋₆ alkylamino, (h) (C₁₋₆ alkyl)₂amino, (i) aryl C₀₋₆alkylamino, (j) (aryl C₀₋₆ alkyl)₂amino, (k) C₁₋₆ alkylthio, (l) arylC₀₋₆alkylthio, (m) C₁₋₆ alkylsulfinyl, (n) aryl C₀₋₆alkylsulfinyl, (o)C₁₋₆ alkylsulfonyl, (p) aryl C₀₋₆alkylsulfonyl, (q) C₁₋₆ alkoxy, (r)aryl C₀₋₆ alkoxy, (s) hydroxycarbonyl, (t) C₁₋₆ alkoxycarbonyl, (u) arylC₀₋₆ alkoxycarbonyl, (v) hydroxycarbonyl C₁₋₆ alkyloxy, (w) hydroxy, (x)cyano, (y) nitro, (z) perfluoroC₁₋₄alkyl, (aa) perfluoroC₁₋₄alkoxy, (bb)oxo, (cc) C₁₋₆ alkylcarbonyloxy, (dd) aryl C₀₋₆alkylcarbonyloxy, (ee)alkyl C₁₋₆ carbonylamino, (ff) aryl C₀₋₆ alkylcarbonylamino, (gg) C₁₋₆alkylsulfonylamino, (hh) aryl C₀₋₆alkylsulfonylamino, (ii) C₁₋₆alkoxycarbonylamino, (jj) aryl C₀₋₆ alkoxycarbonylamino, (kk)C₁₋₆alkylaminocarbonylamino, (ll) aryl C₀₋₆alkylaminocarbonylamino, (mm)(C₁₋₆alkyl)₂ aminocarbonylamino, (nn) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy, (pp) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (qq) spiro-C₃₋₈cycloalkyl; (5) C₃₋₈cycloalkyl, either unsubstituted or substituted with one to 3substituents selected from: (a) halogen, (b) aryl, (c) C₁₋₈ alkyl, (d)C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) aryl C₁₋₆alkyl, (g)amino C₀₋₆alkyl, (h) C₁₋₆ alkylamino C₀₋₆alkyl, (i) (C₁₋₆ alkyl)₂aminoC₀₋₆alkyl, (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (k) (aryl C₀₋₆alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆ alkylthio, (m) aryl C₀₋₆alkylthio, (n)C₁₋₆ alkylsulfinyl, (o) aryl C₀₋₆alkylsulfinyl, (p) C₁₋₆ alkylsulfonyl,(q) aryl C₀₋₆alkylsulfonyl, (r) C₁₋₆ alkoxy C₀₋₆alkyl, (s) aryl C₀₋₆alkoxy C₀₋₆alkyl, (t) hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonylC₀₋₆alkyl, (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonylC₁₋₆ alkyloxy, (x) hydroxy C₀₋₆alkyl, (y) cyano, (z) nitro, (aa)perfluoroC₁₋₄alkyl, (bb) perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆alkylcarbonyloxy, (ee) aryl C₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆carbonylamino, (gg) aryl C₀₋₆ alkylcarbonylamino, (hh) C₁₋₆alkylsulfonylamino, (ii) aryl C₀₋₆alkylsulfonylamino, (jj) C₁₋₆alkoxycarbonylamino, (kk) aryl C₀₋₆ alkoxycarbonylamino, (ll)C₁₋₆alkylaminocarbonylamino, (mm) aryl C₀₋₆alkylaminocarbonylamino, (nn)(C₁₋₆alkyl)₂ aminocarbonylamino, (oo) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (pp) (C₁₋₆alkyl)₂ aminocarbonyloxy, (qq) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, (rr) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and (ss)spiro-C₃₋₈cycloalkyl; (6) cycloheteroalkyl, unsubstituted or substitutedwith one to three substituents selected from: (a) halogen, (b) aryl, (c)C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) arylC₁₋₆alkyl, +P3 (g) amino C₀₋₆alkyl, (h) C₁₋₆ alkylamino C₀₋₆alkyl, (i)(C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (k)(aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆ alkylthio, (m) arylC₀₋₆alkylthio, (n) C₁₋₆ alkylsulfinyl, (o) aryl C₀₋₆alkylsulfinyl, (p)C₁₋₆ alkylsulfonyl, (q) aryl C₀₋₆alkylsulfonyl, (r) C₁₋₆ alkoxyC₀₋₆alkyl, (s) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (t) hydroxycarbonylC₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (v) aryl C₀₋₆alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonyl C₁₋₆ alkyloxy, (x) hydroxyC₀₋₆alkyl, (y) cyano, (z) nitro, (aa) perfluoroC₁₋₄alkyl, (bb)perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆ alkylcarbonyloxy, (ee) arylC₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆ carbonylamino, (gg) aryl C₀₋₆alkylcarbonylamino, (hh) C₁₋₆ alkylsulfonylamino, (ii) arylC₀₋₆alkylsulfonylamino, (jj) C₁₋₆ alkoxycarbonylamino, (kk) aryl C₀₋₆alkoxycarbonylamino, (ll) C₁₋₆alkylaminocarbonylamino, (mm) arylC₀₋₆alkylaminocarbonylamino, (nn) (C₁₋₆alkyl)₂ aminocarbonylamino, (oo)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (pp) (C₁₋₆alkyl)₂aminocarbonyloxy, (qq) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, and (rr)C₀₋₆alkylcarbonyl C₀₋₆alkyl, and (ss) spiro C₃₋₈cycloalkyl provided thatany heteroatom substituent is bonded to a carbon atom in thecycloheteroalkyl ring; R³ is selected from H and C₁₋₈ alkyl, or R² andR³, together with the nitrogen atom to which they are attached, form a5- to 7-membered heterocyclic ring, optionally containing one or twoadditional heteroatoms selected from N, S, and O, optionally having oneor more degrees of unsaturation, optionally fused to a 6-memberedheteroaromatic or aromatic ring, either unsubstituted or substitutedwith one to three substituents selected from: (1) halogen, (2) aryl, (3)C₁₋₈ alkyl, (4) C₃₋₈ cycloalkyl, (5) C₃₋₈ cycloheteroalkyl, (6) arylC₁₋₆alkyl, (7) amino C₀₋₆alkyl, (8) C₁₋₆ alkylamino C₀₋₆alkyl, (9) (C₁₋₆alkyl)₂amino C₀₋₆alkyl, (10) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (11) (arylC₀₋₆ alkyl)₂amino C₀₋₆alkyl, (12) C₁₋₆ alkylthio, (13) arylC₀₋₆alkylthio, (14) C₁₋₆ alkylsulfinyl, (15) aryl C₀₋₆alkylsulfinyl,(16) C₁₋₆ alkylsulfonyl, (17) aryl C₀₋₆alkylsulfonyl, (18) C₁₋₆ alkoxyC₀₋₆alkyl, (19) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (20) hydroxycarbonylC₀₋₆alkyl, (21) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (22) aryl C₀₋₆alkoxycarbonyl C₀₋₆alkyl, (23) hydroxycarbonyl C₁₋₆ alkyloxy, (24)hydroxy C₀₋₆alkyl, (25) cyano, (26) nitro, (27) perfluoroC₁₋₄alkyl, (28)perfluoroC₁₋₄alkoxy, (29) oxo, (30) C₁₋₆ alkylcarbonyloxy, (31) arylC₀₋₆alkylcarbonyloxy, (32) C₁₋₆ alkyl carbonylamino, (33) aryl C₀₋₆alkylcarbonylamino, (34) C₁₋₆ alkylsulfonylamino, (35) arylC₀₋₆alkylsulfonylamino, (36) C₁₋₆ alkoxycarbonylamino, (37) aryl C₀₋₆alkoxycarbonylamino, (38) C₁₋₆alkylaminocarbonylamino, (39) arylC₀₋₆alkylaminocarbonylamino, (40) (C₁₋₆alkyl)₂ aminocarbonylamino, (41)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (42) (C₁₋₆alkyl)₂aminocarbonyloxy, (43) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, and (44)spiro-C₃₋₈cycloalkyl provided that any heteroatom substituent is bondedto a carbon atom in the heterocyclic ring; R⁴ and R⁵ are eachindependently selected from (1) hydrogen, (2) halogen, (3) aryl, (4)C₁₋₈ alkyl, (5) C₃₋₈ cycloalkyl, (6) C₃₋₈ cycloheteroalkyl, (7) arylC₁₋₆alkyl, (8) amino C₀₋₆alkyl, (9) C₁₋₆ alkylamino C₀₋₆alkyl, (10)(C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (11) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (12)(aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (13) C₁₋₆ alkylthio, (14) arylC₀₋₆alkylthio, (15) C₁₋₆ alkylsulfinyl, (16) aryl C₀₋₆alkylsulfinyl,(17) C₁₋₆ alkylsulfonyl, (18) aryl C₀₋₆alkylsulfonyl, (19) C₁₋₆ alkoxyC₀₋₆alkyl, (20) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (21) hydroxycarbonylC₀₋₆alkyl, (22) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (23) aryl C₀₋₆alkoxycarbonyl C₀₋₆alkyl, (24) hydroxycarbonyl C₁₋₆ alkyloxy, (25)hydroxy C₀₋₆alkyl, (26) cyano, (27) nitro, (28) perfluoroC₁₋₄alkyl, (29)perfluoroC₁₋₄alkoxy, (30) C₀₋₆alkylcarbonyl C₀₋₆alkyl, (31) C₁₋₆alkylcarbonyloxy, (32) aryl C₀₋₆alkylcarbonyloxy, (33) C₁₋₆ alkylcarbonylamino, (34) aryl C₀₋₆ alkylcarbonylamino, (35) C₁₋₆alkylsulfonylamino, (36) aryl C₀₋₆alkylsulfonylamino, (37) C₁₋₆alkoxycarbonylamino, (38) aryl C₀₋₆ alkoxycarbonylamino, (39)C₁₋₆alkylaminocarbonylamino, (40) aryl C₀₋₆alkylaminocarbonylamino, (41)(C₁₋₆alkyl)₂ aminocarbonylamino, (42) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (43) (C₁₋₆alkyl)₂ aminocarbonyloxy, and (44) (arylC₀₋₆alkyl)₂ aminocarbonyloxy; or, R⁴ and R⁵ together form an oxo groupor ═CH—R⁶ or a spiro C₃₋₇ cycloalkyl ring, unsubstituted or substitutedwith R⁶; R⁶ is selected from: (1) hydrogen, and (2) C₁₋₄ alkyl; or apharmaceutically acceptable salt thereof.
 5. The method according toclaim 4 wherein the condition is osteoporosis.
 6. The method accordingto claim 4 wherein: R¹ is selected from: (1) C₁₋₂ alkyl, (2) C₃₋₆cycloalkyl and (3) trifluoromethyl; R³ is hydrogen; and R⁴ and R⁵ areeach hydrogen.
 7. The method according to claim 6 wherein: R¹ isselected from, (1) methyl, and (2) cyclopropyl; R² is selected from, (1)aryl, either unsubstituted or substituted with one to three substituentsselected from: (a) halogen, (b) aryl, (c) C₁₋₆alkyl, (d) C₁₋₆alkoxy, (e)cyano, (f) hydroxy, (g) trifluoromethyl, (h) perfluoroC₂₋₄ alkyl, and(i) trifluoromethoxy; (2) C₁₋₆ alkyl, either unsubstituted orsubstituted with one to three substituents selected from: (a) fluoro,(b) aryl, (c) C₅₋₆heteroalkyl, (d) amino, (e) C₁₋₆alkylamino, (f)(C₁₋₆alkyl)₂ amino, (g) C₁₋₄alkoxy, (h) hydroxy, (i) trifluoromethoxy,and (j) oxo; (3) C₃₋₈cycloalkyl, either unsubstituted or substitutedwith one to three substituents selected from: (a) fluoro, (b) C₁₋₄alkyl,(c) trifluoromethyl, (d) aryl, (e) hydroxy, (f) C₁₋₃alkoxy, (g) oxo, and(h) spiro-C₃₋₈cycloalkyl.
 8. The method according to claim 6, wherein:R¹ is selected from, (1) methyl, (2) cyclopropyl, and (3)trifluoromethyl; R² is selected from: (1) aryl, substituted by one tothree substituents selected from: (a) fluoro, (b) chloro, (c) bromo, (d)phenyl, (e) methyl, (f) ethyl, (g) benzyl, (h) amino, (i) cyano, (j)morpholinyl, (k) nitro, (l) methoxy, (m) methylthio, (n) hydroxy, (o)trifluoromethyl, (p) trifluoromethoxy, (q) formyl, (r) acetyl, and (s)oxo; (2) C₁₋₈ alkyl, unsubstituted or substituted with one or twosubstituents independently selected from: (a) fluoro, (b) chloro, (c)phenyl, (d) thienyl, (e) pyrazinyl, (f) C₃₋₆ cycloalkyl, (g) C₅₋₆cycloheteroalkyl, (h) amino, (i) C₁₋₄ alkylamino, (j) (C₁₋₄alkyl)₂amino, (k) benzylamino, (l) phenylamino, (m) (aryl C₀₋₁alkyl)₂amino, (n) methylthio, (o) methoxy, (p) hydroxycarbonyl, (q) C₁₋₆alkoxycarbonyl, (r) phenyl C₀₋₁ alkoxycarbonyl, (s) hydroxy, (t)trifluoromethyl, (u) trifluoromethoxy, (v) oxo, and (w)methylcarbonyloxy (3) perfluoroalkyl selected from trifluromethyl andperfluoroethyl; (4) C₃₋₈ cycloalkyl, either unsubstituted or substitutedwith one to two substituents selected from: (a) fluoro, (b) chloro, (c)phenyl, (d) C₁₋₄ alkyl, (e) cyclopropyl, (f) cyclohexyl, (g) benzyl, (h)amino, (i) C₁₋₃ alkylamino, (j) C₁₋₃ alkoxy, (k) hydroxy, (l)trifluoromethyl, (m) trifluoromethoxy, (n) oxo, (o) methylcarbonyloxy,(p) methylcarbonylamino, (q) methoxycarbonylamino, (r)methylaminocarbonylamino, (s) spiro C₃₋₈ cycloalkyl; (5)cycloheteroalkyl, either unsubstituted or substituted with one to twosubstituents selected from: (a) fluoro, (b) chloro, (c) phenyl, (d) C₁₋₄alkyl, (e) benzyl, (f) amino, (g) C₁₋₃ alkylamino, (h) C₁₋₃ alkoxy, (i)hydroxy, (j) trifluoromethyl, (k) trifluoromethoxy, and (l) oxo;cycloheteroalkyl is selected from: piperidinyl, pyrrolidinyl,morpholinyl and octahydro-2H-quinolizinyl; aryl is selected from phenyl,quinolinyl, pyridyl, pyrazolyl, benzamidazolyl, imidazolyl, furyl,naphthyl, indanyl, thienyl, pyrazinyl, benzothienyl,3,4-dihydro-1(1H)-isoquinolinyl, 1-8-tetrahydronaphthyridinyl,imidazo[1,2-a]pyridinyl, 2-oxo-2,3,4,5-tetrahydro-1H-benzo[B]azepinyl,quinoxalinyl, imidazo[1,2-a]pyrimidinyl, 2-3-cyclopentenopyridinyl,1-(2H)-phthalazinyl, 1,2,3,4-tetrahydroquinolinyl, oxindolyl,isoquinolinyl, imidazo[2,1-b][1,3]thiazolyl,2,3-dihydroimidazo[2,1-b][1,3]thiazolyl, and indolyl; andpharmaceutically acceptable salts thereof.
 9. The method according toclaim 1 wherein the compound is selected from: (1)N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide, (2)N-(2-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(3)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(4)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(5)N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(6)N-(2-biphenyl)-3-oxo-4-methyl-4-aza-50α-androst-1-ene-17β-carboxamide,(7)N-(4-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(8)N-(3-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(9)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(10)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(11)N-(3-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(12)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(13)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(14)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(15)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(16)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(17)N-(2-methyl-4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(18)N-(4-methoxy-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(19)N-(4-chloro-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(20)N-(2,4-dimethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(21)N-(3-bromo-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(22)N-(2,2,2-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(23)N-(2-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(24) N-(butyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(25)N-(5-methyl-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(26)N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(27)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(28)N-(4-bromo-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(29)N-(4-chloro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(30)N-(2,4-dichlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(31)N-(3-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(32)N-(4-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(33)N-(5-fluoro-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(34)N-(5-chloro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(35) N-(benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(36)N-((S)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(37)N-((R)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(38)N-(2-phenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(39)N-(1-(3-phenylpropyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(40)N-(3-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(41)N-(2-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(42)N-(2-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(43)N-(3-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(44)N-(3-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(45)N-(4-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(46)N-(3-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(47)N-(2-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(48)N-(cyclohexylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(49)N-(3-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(50)N-(2-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(51)N-(3-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(52)N-(4-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(53)N-(3-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(54)N-(3-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(55)N-(4-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(56)N-(2-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(57)N-(4-methoxylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(58)N-(4-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(59)N-((R)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(60)N-((S)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(61)N-(3-(1-pyrrolidin-2-one)-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene17β-carboxamide, (62)N-(2-furanylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(63)N-(1-naphthylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(64)N-(2-(4-imidazoylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(65)N-(2-(3-indolylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(66)N-(5-indolyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(67)N-((1,2-methylenedioxy)-4-benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(68)N-(1,2-diphenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(69)N-(2-(1-hydroxy-1-phenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(70)N-(2-(2-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(71)N-(3-(1-imidazolyl)-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(72)N-(2-(2-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(73)N-(2-methoxyethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(74)N-(4-fluoro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(75)N-(2,4-difluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(76)N-(4-fluoro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(77)N-(4-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(78)N-(2-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(79)N-(3-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(80)N-(3,4-difluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(81)N-(4-dimethylaminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(82)N-(2-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(83)N-(2-benzamidazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(84)N-(1-(4-phenylbutyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(85)N-(3,5-dimethoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(86)N-(2-(2-pyridinylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(87)N-(2-methyl-5-pyrazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(88)N-(2-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(89)N-(2-(2-thiophenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(90)N-(1-(1-naphthyl)-1(R)-ethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(91)N-(2-(3-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(92)N-(2-(2-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(93)N-(2-(4-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(94)N-(4-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(95)N-(2-(3-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(96)N-(2-(3,4-methylenedioxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(97)N-(2-thiophenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(98)N-(2-(4-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(99)N-(2-aminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(100)N-(2-(4-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(101) N-((1S, 2R)2-hydroxy-1-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(102)N-(2-dimethylaminoethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(103) N-(phenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(104)N-(2-chlorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(105)N-(2-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(106)N-(2-trifluoromethoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(107)N-(2-methoxyphenyl)-3-oxo-4-ethyl-4-4-aza-5α-androst-1-ene-17β-carboxamide,(108) N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(109)N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(110)N-(1,1,1-trifluoroethyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(111) N-(2-propyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(112)N-(2-biphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(113)N-(2-acetylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(114)N-(3-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(115)N-(2-pyridinyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(116)N-(3-pyridinyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(117)N-(2-methylsulfonylphenyl)-3-oxo,4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(118)N-(2-methylsulfoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(119) N-(phenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(120)N-(2-chlorophenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(121)N-(2-trifluoromethylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(122)N-(3-methylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(123)N-(2-methylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(124)N-(2-cyanophenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17α-carboxamide,(125)N-(2-benzoylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(126)N-(1,1,1-trifluoroethyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(127) N-(phenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,(128)N-(2-chlorophenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,(129)N-(2-trifluoromethylphenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,(130) N-(phenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,(131)N-(2-trifluoromethylphenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,(132)N-(2-chlorophenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,(133)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(134)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(135)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(136)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(137)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(138)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(139) N-(phenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(140)N-(2-methoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(141) N-(2-propyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(142) N-(2-biphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(143) N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(144)N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(145)N-(1,1,1-trifluoroethyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(146)N-(4-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(147)N-(1,1,1-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(148) N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(149)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(150)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(151)N-(4-trifluoromethylphenyl)-3-oxo4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(152)N-(2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(153)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(154)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(155)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(156)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(157)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(158)N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(159)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(160)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(161)N-(phenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(162)N-(2-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(163)N-(2-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(164)N-(3-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(165)N-(3-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(166)N-(4-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(167)N-(2-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(168)N-(4-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(169)N-(3-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(170)N-(4-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(171)N-(2-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(172)N-(3-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(173)N-(4-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,and (174)N-(1,1,1-trifluoroethyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,and pharmaceutically acceptable salts thereof.
 10. The method accordingto claim 9 wherein the compound is selected from: (1)N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide, (2)N-(2-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(3)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(4)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(5)N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(6)N-(2-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(7)N-(4-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(8)N-(3-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(9)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(10)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(11)N-(3-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(12)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(13)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(14)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(15)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(16)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(17)N-(2-methyl-4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(18)N-(4-methoxy-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(19)N-(4-chloro-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(20)N-(2,4-dimethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(21)N-(3-bromo-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(22)N-(2,2,2-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(23)N-(2-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(24) N-(butyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(25)N-(5-methyl-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(26)N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(27)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(28)N-(4-bromo-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(29)N-(4-chloro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(30)N-(2,4-dichlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(31)N-(3-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(32)N-(4-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(33)N-(5-chloro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(34) N-(benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(35)N-((S)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(36)N-((R)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(37)N-(2-phenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(38)N-(1-(3-phenylpropyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(39)N-(3-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(40)N-(2-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(41)N-(2-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(42)N-(3-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(43)N-(3-chlorobenzyl)-3-oxo-4-methyl-4-aza-50α-androst-1-ene-17β-carboxamide,(44)N-(4-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(45)N-(3-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(46)N-(2-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(47)N-(cyclohexylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(48)N-(3-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(49)N-(2-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(50)N-(3-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(51)N-(4-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(52)N-(3-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(53)N-(3-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(54)N-(4-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(55)N-(2-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(56)N-(4-methoxylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(57)N-(4-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(58)N-((R)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(59)N-((S)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(60)N-(2-furanylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(61)N-(1-naphthylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(62)N-(2-(3-indolylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(63)N-(5-indolyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(64)N-((1,2-methylenedioxy)-4-benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(65)N-(1,2-diphenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(66)N-(2-(1-hydroxy-1-phenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(67)N-(2-(2-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(68)N-(2-(2-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17α-carboxamide,(69)N-(2-methoxyethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(70)N-(4-fluoro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(71)N-(2,4-difluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(72)N-(4-fluoro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(73)N-(2-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(74)N-(3-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(75)N-(3,4-difluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(76)N-(4-dimethylaminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(77)N-(2-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(78)N-(2-benzamidazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(79)N-(1-(4-phenylbutyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(80)N-(3,5-dimethoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(81)N-(2-(2-pyridinylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(82)N-(2-methyl-5-pyrazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(83)N-(2-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(84)N-(2-(2-thiophenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(85)N-(2-(3-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(86)N-(2-(2-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(87)N-(2-(4-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(88)N-(2-(4-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(89)N-(2-(3-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(90)N-(2-(3,4-methylenedioxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(91)N-(2-thiophenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(92)N-(2-(4-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(93)N-(2-(2-aminobenzyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(94)N-(2-(4-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17α-carboxamide,(95) N-((1S, 2R)2-hydroxy-1-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(96)N-(2-chlorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(97)N-(2-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(98) N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(99)N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(100)N-(3-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(101)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(102)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(103)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(104)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(105)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(106) N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(107)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(108)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(109)N-(2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(110)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(111)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(112)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(113)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(114)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17α-carboxamide,(115)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(116)N-(phenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(117)N-(3-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(118)N-(3-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(119)N-(2-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(120)N-(3-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(121)N-(2-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(122)N-(3-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17α-carboxamide,11. The method according to claim 10, wherein the compound is selectedfrom: (1)N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide, (2)N-(2-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(3)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17α-carboxamide,(4)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(5)N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(6)N-(2-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(7)N-(4-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(8)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(9)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(10)N-(3-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(11)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(12)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-Carboxamide,(13)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(14)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(15)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(16)N-(2-methyl-4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(17)N-(4-methoxy-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(18)N-(4-chloro-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(19)N-(2,4-dimethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(20)N-(3-bromo-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(21)N-(2,2,2-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(22)N-(2-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(23) N-(butyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(24)N-(5-methyl-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(25)N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(26)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(27)N-(4-bromo-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(28)N-(4-chloro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(29)N-(2,4-dichlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(30)N-(3-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(31)N-(4-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(32)N-(5-chloro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(33) N-(benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(34)N-((S)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(35)N-((R)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(36)N-(2-phenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(37)N-(1-(3-phenylpropyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(38)N-(2-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(39)N-(2-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(40)N-(3-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(41)N-(4-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(42)N-(3-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(43)N-(2-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(44)N-(cyclohexylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(45)N-(3-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(46)N-(2-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(47)N-(3-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(48)N-(4-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(49)N-(3-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(50)N-(3-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(51)N-(4-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(52)N-(2-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(53)N-(4-methoxylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(54)N-(4-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(55)N-((R)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(56)N-((S)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(57)N-(2-furanylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(58)N-(1-naphthylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(59)N-(2-(3-indolylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(60)N-(5-indolyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(61)N-((1,2-methylenedioxy)-4-benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(62)N-(1,2-diphenylethyl)-3-oxo-4-methyl-4-4-aza-5α-androst-1-ene-17β-carboxamide,(63)N-(2-(2-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(64)N-(2-(2-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(65)N-(4-fluoro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(66)N-(2,4-difluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(67)N-(4-fluoro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(68)N-(2-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(69)N-(3-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(70)N-(3,4-difluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(71)N-(4-dimethylaminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(72)N-(2-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(73)N-(2-benzamidazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(74)N-(3,5-dimethoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(75)N-(2-(2-pyridinylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(76)N-(2-methyl-5-pyrazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(77)N-(2-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(78)N-(2-(2-thiophenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(79)N-(2-(3-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(80)N-(2-(2-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(81)N-(2-(4-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(82)N-(2-(4-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(83)N-(2-(3-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(84)N-(2-(3,4-methylenedioxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(85)N-(2-thiophenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(86)N-(2-(4-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(87)N-(2-(2-aminobenzyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(88)N-(2-(4-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(89) N-((1S, 2R)2-hydroxy-1-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(90)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(91)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(92)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(93)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(94)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(95)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(96)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(97)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(98)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(99)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,12. The method according to claim 3 wherein the compound is selectedfrom: (1)N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide, (2)N-(2-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(3)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(4)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(5)N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(6)N-(2-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(7)N-(4-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(8)N-(3-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(9)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(10)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(11)N-(3-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(12)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17-carboxamide,(13)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(14)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(15)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(16)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(17)N-(2-methyl-4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(18)N-(4-methoxy-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(19)N-(4-chloro-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(20)N-(2,4-dimethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(21)N-(3-bromo-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17(3-carboxamide,(22)N-(2,2,2-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(23)N-(2-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(24) N-(butyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(25)N-(5-methyl-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(26)N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(27)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(28)N-(4-bromo-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(29)N-(4-chloro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(30)N-(2,4-dichlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17(3-carboxamide,(31)N-(3-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(32)N-(4-cyanophenyl)-3-oxo-4-methyl4-aza-5α-androst-1-ene-17β-carboxamide,(33)N-(5-fluoro-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(34)N-(5-chloro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(35) N-(benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(36)N-((S)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(37)N-((R)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(38)N-(2-phenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(39)N-(1-(3-phenylpropyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(40)N-(3-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(41)N-(2-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(42)N-(2-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(43)N-(3-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(44)N-(3-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(45)N-(4-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(46)N-(3-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(47)N-(2-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(48)N-(cyclohexylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(49)N-(3-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(50)N-(2-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(51)N-(3-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(52)N-(4-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(53)N-(3-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(54)N-(3-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(55)N-(4-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(56)N-(2-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(57)N-(4-methoxylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(58)N-(4-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(59)N-((R)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(60)N-((S)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(61)N-(3-(1-pyrrolidin-2-one)-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(62)N-(2-furanylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(63)N-(1-naphthylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(64)N-(2-(4-imidazoylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(65)N-(2-(3-indolylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(66)N-(5-indolyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(67)N-((1,2-methylenedioxy)-4-benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(68)N-(1,2-diphenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(69)N-(2-(1-hydroxy-1-phenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(70)N-(2-(2-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(71)N-(3-(1-imidazolyl)-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(72)N-(2-(2-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(73)N-(2-methoxyethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(74)N-(4-fluoro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(75)N-(2,4-difluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(76)N-(4-fluoro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(77)N-(4-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(78)N-(2-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(79)N-(3-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(80)N-(3,4-difluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(81)N-(4-dimethylaminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(82)N-(2-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(83)N-(2-benzamidazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(84)N-(1-(4-phenylbutyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(85)N-(3,5-dimethoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(86)N-(2-(2-pyridinylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(87)N-(2-methyl-5-pyrazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(88)N-(2-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(89)N-(2-(2-thiophenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(90)N-(1-(1-naphthyl)-1(R)-ethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(91)N-(2-(3-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(92)N-(2-(2-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(93)N-(2-(4-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(94)N-(4-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(95)N-(2-(3-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(96)N-(2-(3,4-methylenedioxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(97)N-(2-thiophenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(98)N-(2-(4-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(99)N-(2-aminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(100)N-(2-(4-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(101) N-((1S, 2R)2-hydroxy-1-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(102)N-(2-dimethylaminoethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(103) N-(phenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(104)N-(2-chlorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(105)N-(2-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(106)N-(2-trifluoromethoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(107)N-(2-methoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(108) N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(109)N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(110)N-(1,1,1-trifluoroethyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(111) N-(2-propyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(112)N-(2-biphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(113)N-(2-acetylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(114)N-(3-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(115)N-(2-pyridinyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(116)N-(3-pyridinyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(117)N-(2-methylsulfonylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(118)N-(2-methylsulfoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(119) N-(phenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(120)N-(2-chlorophenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(121)N-(2-trifluoromethylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(122)N-(3-methylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(123)N-(2-methylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(124)N-(2-cyanophenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(125)N-(2-benzoylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(126)N-(1,1,1-trifluoroethyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(127) N-(phenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,(128)N-(2-chlorophenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,(129)N-(2-trifluoromethylphenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,(130) N-(phenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,(131)N-(2-trifluoromethylphenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,(132)N-(2-chlorophenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,(133)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(134)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(135)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(136)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(137)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(138)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(139) N-(phenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(140)N-(2-methoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(141) N-(2-propyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(142) N-(2-biphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(143) N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(144)N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(145)N-(1,1,1-trifluoroethyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(146)N-(4-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(147)N-(1,1,1-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(148) N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(149)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(150)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(151)N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(152)N-(2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(153)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(154)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(155)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(156)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(157)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(158)N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(159)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(160)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(161)N-(phenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(162)N-(2-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(163)N-(2-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(164)N-(3-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(165)N-(3-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(166)N-(4-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(167)N-(2-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(168)N-(4-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(169)N-(3-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(170)N-(4-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(171)N-(2-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(172)N-(3-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(173)N-(4-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,and (174)N-(1,1,1-trifluoroethyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,and pharmaceutically acceptable salts thereof.
 13. The method accordingto claim 12 wherein: (1)N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide, (2)N-(2-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(3)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(4)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(5)N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(6)N-(2-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(7)N-(4-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(8)N-(3-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(9)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(10)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(11)N-(3-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(12)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(13)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(14)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(15)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(16)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(17)N-(2-methyl-4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(18)N-(4-methoxy-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(19)N-(4-chloro-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(20)N-(2,4-dimethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(21)N-(3-bromo-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(22)N-(2,2,2-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(23)N-(2-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(24) N-(butyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(25)N-(5-methyl-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(26)N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(27)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(28)N-(4-bromo-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(29)N-(4-chloro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(30)N-(2,4-dichlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(31)N-(3-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(32)N-(4-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(33)N-(5-chloro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(34) N-(benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(35)N-((S)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(36)N-((R)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(37)N-(2-phenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(38)N-(1-(3-phenylpropyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(39)N-(3-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(40)N-(2-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(41)N-(2-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(42)N-(3-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(43)N-(3-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(44)N-(4-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(45)N-(3-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,,(46)N-(2-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(47)N-(cyclohexylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(48)N-(3-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(49)N-(2-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(50)N-(3-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(51)N-(4-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(52)N-(3-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(53)N-(3-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(54)N-(4-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(55)N-(2-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(56)N-(4-methoxylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(57)N-(4-chlorophenyl)-3-oxo-4-methyl-4-aza-α-androst-1-ene-17β-carboxamide,(58)N-((R)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(59)N-((S)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(60)N-(2-furanylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(61)N-(1-naphthylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(62)N-(2-(3-indolylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(63)N-(5-indolyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(64)N-((1,2-methylenedioxy)-4-benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(65)N-(1,2-diphenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(66)N-(2-(1-hydroxy-1-phenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(67)N-(2-(2-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(68)N-(2-(2-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(69)N-(2-methoxyethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(70)N-(4-fluoro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(71)N-(2,4-difluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(72)N-(4-fluoro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(73)N-(2-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(74)N-(3-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(75)N-(3,4-difluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(76)N-(4-dimethylaminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(77)N-(2-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(78)N-(2-benzamidazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(79)N-(1-(4-phenylbutyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(80)N-(3,5-dimethoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(81)N-(2-(2-pyridinylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(82)N-(2-methyl-5-pyrazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(83)N-(2-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(84)N-(2-(2-thiophenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(b 85)N-(2-(3-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(86)N-(2-(2-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(87)N-(2-(4-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(88)N-(4-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(89)N-(2-(3-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(90)N-(2-(3,4-methylenedioxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(91)N-(2-thiophenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(92)N-(2-(4-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(93)N-(2-(2-aminobenzyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(94)N-(2-(4-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(95) N-((1S, 2R)2-hydroxy-1-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(96)N-(2-chlorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(97)N-(2-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(98) N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(99)N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(100)N-(3-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(101)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(102)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(103)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(104)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(105)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(106) N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(107)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(108)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(109)N-(2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(110)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(111)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(112)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(113)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(114)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(115)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(116)N-(phenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(117)N-(3-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(118)N-(3-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(119)N-(2-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(120)N-(3-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(121)N-(2-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(122)N-(3-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,14. The method according to claim 13, wherein the compound is selectedfrom: (1)N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide, (2)N-(2-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(3)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(4)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(5)N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(6)N-(2-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(7)N-(4-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(8)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(9)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(10)N-(3-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(11)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(12)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(13)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(14)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(15)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(16)N-(2-methyl-4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(17)N-(4-methoxy-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(18)N-(4-chloro-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(19)N-(2,4-dimethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(20)N-(3-bromo-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(21)N-(2,2,2-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(22)N-(2-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(23) N-(butyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(24)N-(5-methyl-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(25)N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(26)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(27)N-(4-bromo-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(28)N-(4-chloro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17βcarboxamide,(29)N-(2,4-dichlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(30)N-(3-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(31)N-(4-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(32)N-(5-chloro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(33) N-(benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(34)N-((S)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(35)N-((R)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(36)N-(2-phenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(37)N-(1-(3-phenylpropyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(38)N-(2-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(39)N-(2-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(40)N-(3-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(41)N-(4-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(42)N-(3-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(43)N-(2-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(44)N-(cyclohexylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(45)N-(3-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(46)N-(2-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(47)N-(3-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(48)N-(4-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(49)N-(3-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(50)N-(3-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(51)N-(4-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(52)N-(2-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(53)N-(4-methoxylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(54)N-(4-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(55)N-((R)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(56)N-((S)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(57)N-(2-furanylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(58)N-(1-naphthylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(59)N-(2-(3-indolylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(60)N-(5-indolyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(61)N-((1,2-methylenedioxy)-4-benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(62)N-(1,2-diphenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(63)N-(2-(2-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(64)N-(2-(2-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(65)N-(4-fluoro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androsts1-ene-17β-carboxamide,(66)N-(2,4-difluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(67)N-(4-fluoro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(68)N-(2-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(69) N-(3-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst--1ene-17β-carboxamide, (70)N-(3m,4-difluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(71)N-(4-dimethylaminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(72)N-(2-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(73)N-(2-benzamidazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(74)N-(3,5-dimethoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(75)N-(2-(2-pyridinylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(76)N-(2-methyl-5-pyrazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(77)N-(2-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(78)N-(2-(2-thiophenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(79)N-(2-(3-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(80)N-(2-(2-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(81)N-(2-(4-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(82)N-(2-(4-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(83)N-(2-(3-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(84)N-(2-(3,4-methylenedioxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(85)N-(2-thiophenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(86)N-(2-(4-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(87)N-(2-(2-aminobenzyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(88)N-(2-(4-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(89) N-((1S, 2R)2-hydroxy-1-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(90)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(91)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(92)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(93)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17-carboxamide,(94)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(95)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(96)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(97)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(98)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(99)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,15. The method according to claim 4 wherein the compound is selectedfrom: (1)N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide, (2)N-(2-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(3)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(4)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(5)N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(6)N-(2-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(7)N-(4-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(8)N-(3-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(9)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(10)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(11)N-(3-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(12)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(13)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(14)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(15)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(16)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(17)N-(2-methyl-4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(18)N-(4-methoxy-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(19)N-(4-chloro-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(20)N-(2,4-dimethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(21)N-(3-bromo-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(22)N-(2,2,2-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(23)N-(2-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(24) N-(butyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(25)N-(5-methyl-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(26)N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(27)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(28)N-(4-bromo-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(29)N-(4-chloro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(30)N-(2,4-dichlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(31)N-(3-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(32)N-(4-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(33)N-(5-fluoro-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(34)N-(5-chloro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(35) N-(benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(36)N-((S)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(37)N-((R)-(x-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(38)N-(2-phenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(39)N-(1-(3-phenylpropyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(40)N-(3-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(41)N-(2-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(42)N-(2-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(43)N-(3-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(44)N-(3-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(45)N-(4-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(46)N-(3-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(47)N-(2-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(48)N-(cyclohexylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(49)N-(3-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(50)N-(2-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(51)N-(3-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(52)N-(4-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(53)N-(3-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(54)N-(3-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(55)N-(4-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(56)N-(2-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(57)N-(4-methoxylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(58)N-(4-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(59)N-((R)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(60)N-((S)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(61)N-(3-(1-pyrrolidin-2-one)-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(62)N-(2-furanylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(63) N-(l-naphthylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(64)N-(2-(4-imidazoylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(65)N-(2-(3-indolylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(66)N-(5-indolyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(67)N-((1,2-methylenedioxy)-4-benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(68)N-(1,2-diphenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(69)N-(2-(1-hydroxy-1-phenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(70)N-(2-(2-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(71)N-(3-(1-imidazolyl)-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(72)N-(2-(2-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(73)N-(2-methoxyethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(74)N-(4-fluoro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17βcarboxamide,(75)N-(2,4-difluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(76)N-(4-fluoro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(77)N-(4-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(78)N-(2-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(79)N-(3-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5-androst-1-ene-17β-carboxamide,(80)N-(3,4-difluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(81)N-(4-dimethylaminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(82) N-(2-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17βcarboxamide,(83)N-(2-benzamidazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(84)N-(1-(4-phenylbutyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(85)N-(3,5-dimethoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(86)N-(2-(2-pyridinylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(87)N-(2-methyl-5-pyrazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(88)N-(2-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(89)N-(2-(2-thiophenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(90)N-(1-(1-naphthyl)-1(R)-ethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(91)N-(2-(3-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(92)N-(2-(2-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(93)N-(2-(4-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(94)N-(4-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(95)N-(2-(3-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(96)N-(2-(3,4-methylenedioxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst1-ene-17β-carboxamide, (97)N-(2-thiophenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(98)N-(2-(4-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(99)N-(2-aminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(100)N-(2-(4-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(101) N-((I S, 2R)2-hydroxy-1-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(102)N-(2-dimethylaminoethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(103) N-(phenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(104)N-(2-chlorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(105)N-(2-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(106)N-(2-trifluoromethoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(107)N-(2-methoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(108) N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(109)N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(110)N-(1,1,1-trifluoroethyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(111) N-(2-propyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(112)N-(2-biphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17-carboxamide,(113)N-(2-acetylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(114)N-(3-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(115)N-(2-pyridinyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(116)N-(3-pyridinyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(117)N-(2-methylsulfonylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(118)N-(2-methylsulfoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(119) N-(phenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(120)N-(2-chlorophenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(121)N-(2-trifluoromethylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(122)N-(3-methylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(123)N-(2-methylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(124) N-(2-cyanophenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide, (125)N-(2-benzoylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(126)N-(1,1,1-trifluoroethyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(127) N-(phenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,(128)N-(2-chlorophenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,(129)N-(2-trifluoromethylphenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,(130) N-(phenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,(131)N-(2-trifluoromethylphenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,(132)N-(2-chlorophenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,(133)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(134)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(135)N-(4-trifluoromethoxyphenyl)-3-ox₉-4-methyl-4-aza-5α-androstane-17β-carboxamide,(136)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(137)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(138)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(139) N-(phenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(140)N-(2-methoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(141) N-(2-propyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(142) N-(2-biphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(143) N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(144)N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(145)N-(1,1,1-trifluoroethyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(146)N-(4-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(147)N-(1,1,1-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(148) N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(149)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(150)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(151)N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(152)N-(2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(153)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(154)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(155)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(156)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(157)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(158)N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(159)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(160)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(161)N-(phenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(162)N-(2-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(163)N-(2-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(164)N-(3-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(165)N-(3-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(166)N-(4-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(167)N-(2-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(168)N-(4-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(169)N-(3-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(17)N-(4-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(17β)N-(2-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(172)N-(3-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(173)N-(4-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,and (174)N-(1,1,1-trifluoroethyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,and pharmaceutically acceptable salts thereof.
 16. The method accordingto claim 15 wherein the compound is selected from: (1)N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide, (2)N-(2-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(3)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(4)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(5)N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(6)N-(2-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(7)N-(4-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(8)N-(3-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(9)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(10)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(11)N-(3-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(12)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(13)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(14)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(15)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(16)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(17)N-(2-methyl-4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(18)N-(4-methoxy-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(19)N-(4-chloro-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(20)N-(2,4-dimethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(21)N-(3-bromo-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(22)N-(2,2,2-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(23)N-(2-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(24) N-(butyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(25)N-(5-methyl-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(26)N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(27)N-(3-fluorophenyl)-3-oxo-4-methyl4-aza-5α-androst-1-ene-17β-carboxamide,(28)N-(4-bromo-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(29)N-(4-chloro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(30)N-(2,4-dichlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(31)N-(3-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(32)(N-(4-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(33)N-(5-chloro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(34) (N-(benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(35)N-((S)-a-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(36)N-((R)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(37)(N-(2-phenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(38)(N-(1-(3-phenylpropyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(39)(N-(3-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(40)N-(2-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(41)(N-(2-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(42)N-(3-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(43)(N-(3-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(44)(N-(4-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(45)(N-(3-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(46)(N-(2-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(47)(N-(cyclohexylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(48)N-(3-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(49)(N-(2-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(50)(N-(3-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(51)(N-(4-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(52)N-(3-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(53)N-(3-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(54)N-(4-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(55)N-(2-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(56)N-(4-methoxylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(57)N-(4-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(58)N-((R)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(59)N-((S)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(60)N-(2-furanylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(61)N-(1-naphthylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(62)N-(2-(3-indolylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(63)N-(5-indolyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(64)N-((1,2-methylenedioxy)-4-benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(65)N-(1,2-diphenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(66)N-(2-(1-hydroxy-1-phenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(67)N-(2-(2-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(68)N-(2-(2-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(69)N-(2-methoxyethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(70)N-(4-fluoro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(71)N-(2,4-difluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(72)N-(4-fluoro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(73)N-(2-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(74)N-(3-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(75)N-(3,4-difluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(76)N-(4-dimethylaminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(77)N-(2-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(78)N-(2-benzamidazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(79)N-(1-(4-phenylbutyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(80)N-(3,5-dimethoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(81)N-(2-(2-pyridinylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(82)N-(2-methyl-5-pyrazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(83)N-(2-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(84)N-(2-(2-thiophenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(85)N-(2-(3-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(86)N-(2-(2-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(87)N-(2-(4-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(88)N-(4-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(89)N-(2-(3-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(90)N-(2-(3,4-methylenedioxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(91)N-(2-thiophenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(92)N-(2-(4-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(93)N-(2-(2-aminobenzyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(94)N-(2-(4-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(95) N-((1S, 2R)2-hydroxy-1-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17-carboxamide,(96)N-(2-chlorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(97)N-(2-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(98) N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(99)N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(100)N-(3-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(101)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(102)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(103)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(104)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(105)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(106) N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(107)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(108)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(109)N-(2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(110)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(111)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(112)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(113)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(114)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(115)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(116)N-(phenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(117)N-(3-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(118)N-(3-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(119)N-(2-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(120)N-(3-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(121)N-(2-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(122)N-(3-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,17. The method according to claim 16, wherein the compound is selectedfrom: (1)N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide, (2)N-(2-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(3)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(4)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(5)N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(6)N-(2-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(7)N-(4-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(8)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(9)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(10)(N-(3-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(11)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(12)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(13)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(14)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(15)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(16)N-(2-methyl-4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(17)N-(4-methoxy-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(18)N-(4-chloro-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(19)N-(2,4-dimethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(20)N-(3-bromo-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(21)N-(2,2,2-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(22)N-(2-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(23) N-(butyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(24)N-(5-methyl-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(25)N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(26)N-(3-fluorophenyl)-3-oxo-4-methyl14-aza-5α-androst-1-ene-17β-carboxamide,(27)N-(4-bromo-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(28)N-(4-chloro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(29)N-(2,4-dichlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(30)N-(3-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(31)N-(4-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(32)N-(5-chloro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(33) N-(benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(34)N-((S)-(x-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(35)N-((R)-(α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(36)N-(2-phenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(37)N-(1-(3-phenylpropyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(38)N-(2-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(39)N-(2-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(40)N-(3-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(41)N-(4-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(42)N-(3-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(43)N-(2-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(44)N-(cyclohexylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(45)N-(3-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(46)N-(2-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(47)N-(3-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(48)N-(4-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(49)N-(3-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(50)N-(3-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(51)N-(4-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(52)N-(2-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(53)N-(4-methoxylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(54)N-(4-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(55)N-((R)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(56)N-((S)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(57)N-(2-furanylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(58)N-(1-naphthylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(59)N-(2-(3-indolylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(60)N-(5-indolyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(61)N-((1,2-methylenedioxy)-4-benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(62)N-(1,2-diphenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(63)N-(2-(2-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(64)N-(2-(2-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(65)N-(4-fluoro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(66)N-(2,4-difluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(67)N-(4-fluoro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(68)N-(2-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(69)N-(3-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(70)N-(3,4-difluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(71)N-(4-dimethylaminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(72)N-(2-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(73)N-(2-benzamidazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(74)N-(3,5-dimethoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(75)N-(2-(2-pyridinylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(76)N-(2-methyl-5-pyrazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(77)N-(2-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(78)N-(2-(2-thiophenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(79)N-(2-(3-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(80)N-(2-(2-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(81)N-(2-(4-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(82)N-(4-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(83)N-(2-(3-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(84)N-(2-(3,4-methylenedioxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(85)N-(2-thiophenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(86)N-(2-(4-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(87)N-(2-(2-aminobenzyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(88)N-(2-(4-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(89) N-((1S, 2R)2-hydroxy-1-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(90)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(91)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(92)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(93)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(94)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(95)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(96)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(97)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(98)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,and (99)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide.18. The method according to claim 1, wherein the androgen-dependentcondition is osteoporosis.
 19. The method according to claim 18,additionally comprising the administration of a bone-strengthening agentselected from: (a) estrogen or an estrogen derivative, alone or incombination with a progestin or progestin derivative, (b) abisphosphonate, (c) an antiestrogen or a selective estrogen receptormodulator, (d) an osteoclast integrin inhibitor, (e) a cathepsin Kinhibitor, (f) an HMG-CoA reductase inhibitor, (g) an osteoclastvacuolar ATPase inhibitor, (h) an antagonist of VFGF binding toosteoclast receptors, (i) a peroxisome proliferator-activated receptorγ, (j) calcitonin, (k) a calcium receptor antagonist, (l) parathyroidhormone, (m) a growth hormone secretagogue, (n) human growth hormone,(o) insulin-like growth factor, (p) a P-38 protein kinase inhibitor, (q)bone morphogenic protein, (r) an inhibitor of BMP antagonism, (s) aprostaglandin derivative, (t) vitamin D or vitamin D derivative, (u)vitamin K or vitamin K derivative, (v) ipriflavone, (w) fluoride salts,and (x) dietary calcium supplement.
 20. The method according to claim19, wherein: (a) the estrogen or estrogen derivative, alone or incombination with a progestin or progestin derivative is selected from:conjugated estrogen, equine estrogen, 17β-estradiol, estrone,17β-ethynyl estradiol, alone or in combination with an agent selectedfrom norethindrone and medroxyprogesterone acetate; (b) thebisphosphonate is selected from: (1)4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid, (2)N-methyl-4-amino-hydroxybutylidene-1,1-bisphosphonic acid, (3)4-(N,N-dimethylamino-1-hydroxybutylidene-1,1-bisphosphonic acid, (4)3-amino-1-hydroxypropylidene-1,1-bisphosphonic acid, (5)3-(N,N-dimethylamino)-1-hydroxypropylidene-1,1-bisphosphonic acid, (6)1-hydroxy-3-(N-methyl-N-pentylamino)propylidene-1,1-bisphosphonic acid,(7) 1-hydroxy-2-(3-pyridyl)ethylidene-1,1-bisphosphonic acid, (8)4-(hydroxymethylene-1,1-bisphosphonic acid)piperidine, (9)(1-hydroxyethylidene)-bisphosphonate, (10)(dichloromethylene)-bisphosphonate, (11)[1-hydroxy-2-imidazopyridin-(1,2-a)-3-ylethylidene] bisphosphonate, (12)(6-amino-1-hydroxyhexylidene)bisphosphonate, and (13)[1-hydroxy-2-(1H-imidazole-1-yl)ethylidene]bisphosphonate; (c) theantiestrogen or selective estrogen receptor modulator is selected from:raloxifene, clomiphene, zuclomiphene, enclomiphene, nafoxidene, CI-680,CI-628, CN-55,945-27, Mer-25, U-11, 555A, U-100A tamoxifen,lasofoxifene, toremifene, azorxifene, EM-800, EM-652, TSE 424,droloxifene, idoxifene, and levormeloxifene; (d) the osteoclast integrininhibitor is selected from an alphavbeta3 inhibitor or mixed alphavbeta₃and alphavbeta₅ inhibitor; (e) the HMG-CoA reductase inhibitor isselected from lovastatin, simvastatin, dihydroxy-open acid simvastatin,pravastatin, fluvastatin, atorvastatin, cerivastatin, rosuvastatin,pitavastatin, and nisvastatin; (f) calcitonin is salmon calcitoninadmininstered as a nasal spray; (g) bone morphogenic protein is selectedfrom BMP 2, BMP 3, BMP 5, BMP 6, BMP 7, TGF beta, and GDF5; (h)insulin-like growth factor is selected from IGF I and IGF II alone or incombination with IGF binding protein 3; (i) the prostaglandin derivativeis selected from agonists of prostaglandin receptor EP1, EP2, EP4, FP,and IP; (j) the fibroblast growth factor is selected from aFGF and bFGF;(k) parathyroid hormone or parathyroid hormone analog is selected fromparathyroid hormone subcutaneous injection, human PTH, 1-84, 1-34 andother partial sequences, native or with substitutions; (l) vitamin D orvitamin D derivative is selected from: natural vitamin D, 25-OH-vitaminD3, 1α,25(OH)₂ vitamin D3, 1α-OH-vitamin D3, 1α-OH-vitamin D2,dihydrotachysterol, 26,27-F6-1α,25(OH)2 vitamin D3, 19-nor-1α,25(OH)₂vitamin D3, 22-oxacalcitriol, calcipotriol,1α,25(OH)₂-16-ene-23-yne-vitamin D3 (Ro 23-7553), EB1089,20-epi-1α,25(OH)₂ vitamin D3, KH1060, ED71, 1α,24(S)-(OH)₂ vitamin D3,and 1α,24(R)-(OH)2 vitamin D3; (m) the dietary calcium supplement isselected from calcium carbonate, calcium citrate, and natural calciumsalts; (n) the fluoride salts are selected from: sodium fluoride andmonosodium fluorophosphate (MFP); and pharmaceutically acceptable saltsthereof.
 21. The method according to claim 18, additionally comprisingthe administration of 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acidmonosodium salt, trihydrate.
 22. The method according to claim 18wherein the compound of structural formula I is selected from: (1)N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide, (2)N-(2-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(3)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(4)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(5)N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(6)N-(2-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(7)N-(4-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(8)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(9)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(10)N-(3-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(I1)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(12)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(13)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(14)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(15)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(16)N-(2-methyl-4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(17)N-(4-methoxy-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17-carboxamide,(18)N-(4-chloro-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(19)N-(2,4-dimethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(20)N-(3-bromo-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(21)N-(2,2,2-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(22)N-(2-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(23) N-(butyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(24)N-(5-methyl-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(25)N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-I1-ene-17β-carboxamide,(26)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(27)N-(4-bromo-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(28)N-(4-chloro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(29)N-(2,4-dichlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(30)N-(3-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(31)N-(4-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(32)N-(5-chloro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(33) N-(benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(34)N-((S)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(35)N-((R)-α-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(36)N-(2-phenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(37)N-(1-(3-phenylpropyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(38)N-(2-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(39)N-(2-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(40)N-(3-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(41)N-(4-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(42)N-(3-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(43)N-(2-methoxybenzyl)-3-oxo-4-methyl-4-aza-5∘-androst-1-ene-17β-carboxamide,(44)N-(cyclohexylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(45)N-(3-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(46)N-(2-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(47)N-(3-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(48)N-(4-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(49)N-(3-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(50)N-(3-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(51)N-(4-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(52)N-(2-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(53)N-(4-methoxylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(54)N-(4-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(55)N-((R)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(56)N-((S)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(57)N-(2-furanylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(58)N-(1-naphthylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(59)N-(2-(3-indolylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(60)N-(5-indolyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(61)N-((1,2-methylenedioxy)-4-benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(62)N-(1,2-diphenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(63)N-(2-(2-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(64)N-(2-(2-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(65)N-(4-fluoro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(66)N-(2,4-difluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(67)N-(4-fluoro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(68)N-(2-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(69)N-(3-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(70)N-(3,4-difluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(71)N-(4-dimethylaminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(72)N-(2-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(73)N-(2-benzamidazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(74)N-(3,5-dimethoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(75)N-(2-(2-pyridinylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(76)N-(2-methyl-5-pyrazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(77)N-(2-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(78)N-(2-(2-thiophenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(79)N-(2-(3-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(80)N-(2-(2-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(81)N-(2-(4-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(82)N-(2-(4-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(83)N-(2-(3-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(84)N-(2-(3,4-methylenedioxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(85)N-(2-thiophenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(86)N-(2-(4-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(87)N-(2-(2-aminobenzyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(88)N-(2-(4-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(89) N-((1S, 2R)2-hydroxy-1-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(90)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(91)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(92)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(93)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(94)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5β-androst-5-ene-17β-carboxamide,(95)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(96)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(97)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(98)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(99)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,and pharmaceutically acceptable salts thereof.
 23. A compositioncomprising a compound of structural formula I

wherein: “a” and “b” are independently selected from a single bond and adouble bond; R¹ is selected from: (1) C₁₋₃ alkyl, (2) C₂₋₃ alkenyl, (3)C₃₋₆ cycloalkyl, (4) C₁₋₃ alkyl wherein one or more of the hydrogenatoms has been replaced with a fluorine atom, (5) aryl, and (6)aryl-C₁₋₃ alkyl; R² is selected from: (1) aryl, either unsubstituted orsubstituted with one to three substituents selected from: (a) halogen,(b) aryl, (c) C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈cycloheteroalkyl, (f) aryl C₁₋₆alkyl, (g) amino C₀₋₆alkyl, (h) C₁₋₆alkylamino C₀₋₆alkyl, (i) (C₁₋₆ alkyl)2amino C₀₋₆alkyl, (j) aryl C₀₋₆alkylamino C₀₋₆alkyl, (k) (aryl C₀₋₆ alkyl)2amino C₀₋₆alkyl, (l) C₁₋₆alkylthio, (m) aryl C₀₋₆alkylthio, (n) C₁₋₆ alkylsulfinyl, (o) arylC₀₋₆alkylsulfinyl, (p) C₁₋₆ alkylsulfonyl, (q) aryl C₀₋₆alkylsulfonyl,(r) C₁₋₆ alkoxy C₀₋₆alkyl, (s) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (t)hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (v) arylC₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonyl C₁₋₆ alkyloxy, (x)hydroxy C₀₋₆alkyl, (y) cyano, (z) nitro, (aa) perfluoroC₁₋₄alkyl, (bb)perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆ alkylcarbonyloxy, (ee) arylC₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆ carbonylamino, (gg) aryl C₀₋₆alkylcarbonylamino, (hh) C₁₋₆ alkylsulfonylamino, (ii) arylC₀₋₆alkylsulfonylamino, (jj) C₁₋₆ alkoxycarbonylamino, (kk) aryl C₀₋₆alkoxycarbonylamino, (ll) C₁₋₆alkylaminocarbonylamino, (mm) arylC₀₋₆alkylaminocarbonylamino, (nn) (C₁₋₆alkyl)₂ aminocarbonylamino, (oo)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (pp) (C₁₋₆alkyl)₂aminocarbonyloxy, (qq) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, (rr)C₀₋₆alkylcarbonyl C₀₋₆alkyl, and (ss) aryl C₀₋₆alkylcarbonyl C₀₋₆alkyl;(2) C₁₋₈ alkyl, unsubstituted or substituted with one to threesubstituents independently selected from: (a) halogen, (b) aryl, (c)C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) amino,(g) C₁₋₆ alkylamino, (h) (C₁₋₆ alkyl)₂amino, (i) aryl C₀₋₆ alkylamino,(j) (aryl C₀₋₆ alkyl)₂amino, (k) C₁₋₆ alkylthio, (l) aryl C₀₋₆alkylthio,(m) C₁₋₆ alkylsulfinyl, (n) aryl C₀₋₆alkylsulfinyl, (o) C₁₋₆alkylsulfonyl, (p) aryl C₀₋₆alkylsulfonyl, (q) C₁₋₆ alkoxy, (r) arylC₀₋₆ alkoxy, (s) hydroxycarbonyl, (t) C₁₋₆ alkoxycarbonyl, (u) aryl C₀₋₆alkoxycarbonyl, (v) hydroxycarbonyl C₁₋₆ alkyloxy, (w) hydroxy, (x)cyano, (y) nitro, (z) perfluoroC₁₋₄alkyl, (aa) perfluoroC₁₋₄alkoxy, (bb)oxo, (cc) C₁₋₆ alkylcarbonyloxy, (dd) aryl C₀₋₆alkylcarbonyloxy, (ee)alkyl C₁₋₆ carbonylamino, (ff) aryl C₀₋₆ alkylcarbonylamino, (gg) C₁₋₆alkylsulfonylamino, (hh) aryl C₀₋₆alkylsulfonylamino, (ii) C₁₋₆alkoxycarbonylamino, (j) aryl C₀₋₆ alkoxycarbonylamino, (kk)C₁₋₆alkylaminocarbonylamino, (ll) aryl C₀₋₆alkylaminocarbonylamino, (mm)(C₁₋₆alkyl)₂ aminocarbonylamino, (nn) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy, (pp) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (qq) spiro-C₃₋₈-cycloalkyl; (3)perfluoroC₁₋₈ alkyl, (4) C₂₋₈ alkenyl, unsubstituted or substituted withone to three substituents independently selected from: (a) halogen, (b)aryl, (c) C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl,(f) amino, (g) C₁₋₆ alkylamino, (h) (C₁₋₆ alkyl)₂amino, (i) aryl C₀₋₆alkylamino, (j) (aryl C₀₋₆ alkyl)₂amino, (k) C₁₋₆ alkylthio, (l) arylC₀₋₆alkylthio, (m) C₁₋₆ alkylsulfinyl, (n) aryl C₀₋₆alkylsulfinyl, (o)C₁₋₆ alkylsulfonyl, (p) aryl C₀₋₆alkylsulfonyl, (q) C₁₋₆ alkoxy, (r)aryl C₀₋₆ alkoxy, (s) hydroxycarbonyl, (t) C₁₋₆ alkoxycarbonyl, (u) arylC₀₋₆ alkoxycarbonyl, (v) hydroxycarbonyl C₁₋₆ alkyloxy, (w) hydroxy, (x)cyano, (y) nitro, (z) perfluoroC₁₋₄alkyl, (aa) perfluoroC₁₋₄alkoxy, (bb)oxo, (cc) C₁₋₆ alkylcarbonyloxy, (dd), aryl C₀₋₆alkylcarbonyloxy, (ee)alkyl C₁₋₆ carbonylamino, (ff) aryl C₀₋₆ alkylcarbonylamino, (gg) C₁₋₆alkylsulfonylamino, (hh) aryl C₀₋₆alkylsulfonylamino, (ii) C₁₋₆alkoxycarbonylamino, (j) aryl C₀₋₆ alkoxycarbonylamino, (kk)C₁₋₆alkylaminocarbonylamino, (ll) aryl C₀₋₆alkylaminocarbonylamino, (mm)(C₁₋₆alkyl)₂ aminocarbonylamino, (nn) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy, (pp) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (qq) spiro-C₃₋₈cycloalkyl; (5) C₃₋₈cycloalkyl, either unsubstituted or substituted with one to 3substituents selected from: (a) halogen, (b) aryl, (c) C₁₋₈ alkyl, (d)C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) aryl C₁₋₆alkyl, (g)amino C₀₋₆alkyl, (h) C₁₋₆ alkylamino C₀₋₆alkyl, (i) (C₁₋₆ alkyl)₂aminoC₀₋₆alkyl, (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (k) (aryl C₀₋₆alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆ alkylthio, (m) aryl C₀₋₆alkylthio, (n)C₁₋₆ alkylsulfinyl, (o) aryl C₀₋₆alkylsulfinyl, (p) C₁₋₆ alkylsulfonyl,(q) aryl C₀₋₆alkylsulfonyl, (r) C₁₋₆ alkoxy C₀₋₆alkyl, (s) aryl C₀₋₆alkoxy C₀₋₆alkyl, (t) hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonylC₀₋₆alkyl, (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonylC₁₋₆ alkyloxy, (x) hydroxy C₀₋₆alkyl, (y) cyano, (z) nitro, (aa)perfluoroC₁₋₄alkyl, (bb) perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆alkylcarbonyloxy, (ee) aryl C₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆carbonylamino, (gg) aryl C₀₋₆ alkylcarbonylamino, (hh) C₁₋₆alkylsulfonylamino, (ii) aryl C₀₋₆alkylsulfonylamino, (jj) C₁₋₆alkoxycarbonylamino, (kk) aryl C₀₋₆ alkoxycarbonylamino, (ll)C₁₋₆alkylaminocarbonylamino, (mm) aryl C₀₋₆alkylaminocarbonylamino, (nn)(C₁₋₆alkyl)₂ aminocarbonylamino, (oo) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (pp) (C₁₋₆alkyl)₂ aminocarbonyloxy, (qq) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, (rr) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and (ss)spiro-C₃₋₈cycloalkyl; (6) cycloheteroalkyl, unsubstituted or substitutedwith one to three substituents selected from: (a) halogen, (b) aryl, (c)C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) arylC₁₋₆alkyl, (g) amino C₀₋₆alkyl, (h) C₁₋₆ alkylamino C₀₋₆alkyl, (i) (C₁₋₆alkyl)₂amino C₀₋₆alkyl, (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (k) (arylC₀₋₆ alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆ alkylthio, (m) aryl C₀₋₆alkylthio,(n) C₁₋₆ alkylsulfinyl, (o) aryl C₀₋₆alkylsulfinyl, (p) C₁₋₆alkylsulfonyl, (q) aryl C₀₋₆alkylsulfonyl, (r) C₁₋₆ alkoxy C₀₋₆alkyl,(s) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (t) hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆alkoxycarbonyl C₀₋₆alkyl, (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w)hydroxycarbonyl C₁₋₆ alkyloxy, (x) hydroxy C₀₋₆alkyl, (y) cyano, (z)nitro, (aa) perfluoroC₁₋₄alkyl, (bb) perfluoroC₁₋₄alkoxy, (cc) oxo, (dd)C₁₋₆ alkylcarbonyloxy, (ee) aryl C₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆carbonylamino, (gg) aryl C₀₋₆ alkylcarbonylamino, (hh) C₁₋₆alkylsulfonylamino, (ii) aryl C₀₋₆alkylsulfonylamino, (j) C₁₋₆alkoxycarbonylamino, (kk) aryl C₀₋₆ alkoxycarbonylamino, (ll)C₁₋₆alkylaminocarbonylamino, (mm) aryl C₀₋₆alkylaminocarbonylamino, (nn)(C₁₋₆alkyl)₂ aminocarbonylamino, (oo) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (pp) (C₁₋₆alkyl)₂ aminocarbonyloxy, (qq) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (rr) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and(ss) spiro C₃₋₈cycloalkyl provided that any heteroatom substituent isbonded to a carbon atom in the cycloheteroalkyl ring; R³ is selectedfrom H and C₁₋₈ alkyl, or R² and R³, together with the nitrogen atom towhich they are attached, form a 5- to 7-membered heterocyclic ring,optionally containing one or two additional heteroatoms selected from N,S, and O, optionally having one or more degrees of unsaturation,optionally fused to a 6-membered heteroaromatic or aromatic ring, eitherunsubstituted or substituted with one to three substituents selectedfrom: (1) halogen, (2) aryl, (3) C₁₋₈ alkyl, (4) C₃₋₈ cycloalkyl, (5)C₃₋₈ cycloheteroalkyl, (6) aryl C₁₋₆alkyl, (7) amino C₀₋₆alkyl, (8) C₁₋₆alkylamino C₀₋₆alkyl, (9) (C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (10) aryl C₀₋₆alkylamino C₀₋₆alkyl, (11) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (12) C₁₋₆alkylthio, (13) aryl C₀₋₆alkylthio, (14) C₁₋₆ alkylsulfinyl, (15) arylC₀₋₆alkylsulfinyl, (16) C₁₋₆ alkylsulfonyl, (17) aryl C₀₋₆alkylsulfonyl,(18) C₁₋₆ alkoxy C₀₋₆alkyl, (19) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (20)hydroxycarbonyl C₀₋₆alkyl, (21) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (22) arylC₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (23) hydroxycarbonyl C₁₋₆ alkyloxy, (24)hydroxy C₀₋₆alkyl, (25) cyano, (26) nitro, (27) perfluoroC₁₋₄alkyl, (28)perfluoroC₁₋₄alkoxy, (29) oxo, (30) C₁₋₆ alkylcarbonyloxy, (31) arylC₀₋₆alkylcarbonyloxy, (32) C₁₋₆ alkyl carbonylamino, (33) aryl C₀₋₆alkylcarbonylamino, (34) C₁₋₆ alkylsulfonylamino, (35) arylC₀₋₆alkylsulfonylamino, (36) C₁₋₆ alkoxycarbonylamino, (37) aryl C₀₋₆alkoxycarbonylamino, (38) C₁₋₆alkylaminocarbonylamino, (39) arylC₀₋₆alkylaminocarbonylamino, (40) (C₁₋₆alkyl)₂ aminocarbonylamino, (41)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (42) (C₁₋₆alkyl)₂aminocarbonyloxy, (43) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, and (44)spiro-C₃₋₈cycloalkyl provided that any heteroatom substituent is bondedto a carbon atom in the heterocyclic ring; R⁴ and R⁵ are eachindependently selected from (1) hydrogen, (2) halogen, (3) aryl, (4)C₁₋₈ alkyl, (5) C₃₋₈ cycloalkyl, (6) C₃₋₈ cycloheteroalkyl, (7) arylC₁₋₆alkyl, (8) amino C₀₋₆alkyl, (9) C₁₋₆ alkylamino C₀₋₆alkyl, (10)(C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (11) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (12)(aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (13) C₁₋₆ alkylthio, (14) arylC₀₋₆alkylthio, (15) C₁₋₆ alkylsulfinyl, (16) aryl C₀₋₆alkylsulfinyl,(17) C₁₋₆ alkylsulfonyl, (18) aryl C₀₋₆alkylsulfonyl, (19) C₁₋₆ alkoxyC₀₋₆alkyl, (20) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (21) hydroxycarbonylC₀₋₆alkyl, (22) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (23) aryl C₀₋₆alkoxycarbonyl C₀₋₆alkyl, (24) hydroxycarbonyl C₁₋₆ alkyloxy, (25)hydroxy C₀₋₆alkyl, (26) cyano, (27) nitro, (28) perfluoroC₁₋₄alkyl, (29)perfluoroC₁₋₄alkoxy, (30) C₀₋₆alkylcarbonyl C₀₋₆alkyl, (31) C₁₋₆alkylcarbonyloxy, (32) aryl C₀₋₆alkylcarbonyloxy, (33) C₁₋₆ alkylcarbonylamino, (34) aryl C₀₋₆ alkylcarbonylamino, (35) C₁₋₆alkylsulfonylamino, (36) aryl C₀₋₆alkylsulfonylamino, (37) C₁₋₆alkoxycarbonylamino, (38) aryl C₀₋₆ alkoxycarbonylamino, (39)C₁₋₆alkylaminocarbonylamino, (40) aryl C₀₋₆alkylaminocarbonylamino, (41)(C₁₋₆alkyl)₂ aminocarbonylamino, (42) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (43) (C₁₋₆alkyl)₂ aminocarbonyloxy, and (44) (arylC₀₋₆alkyl)₂ aminocarbonyloxy; or, R⁴ and R⁵ together form an oxo groupor ═CH—R⁶ or a spiro C₃₋₇ cycloalkyl ring, unsubstituted or substitutedwith R⁶; R⁶ is selected from: (1) hydrogen, and (2) C₁₋₄ alkyl; or apharmaceutically acceptable salt thereof. and a bone-strengthening agentselected from: (a) estrogen or an estrogen derivative, alone or incombination with a progestin or progestin derivative, (b) abisphosphonate, (c) an antiestrogen or a selective estrogen receptormodulator, (d) an osteoclast integrin inhibitor, (e) a cathepsin Kinhibitor, (f) an HMG-CoA reductase inhibitor, (g) an osteoclastvacuolar ATPase inhibitor, (h) an antagonist of VEGF binding toosteoclast receptors, (i) a peroxisome proliferator-activated receptorγ, (j) calcitonin, (k) a calcium receptor antagonist, (l) parathyroidhormone, (m) a growth hormone secretagogue, (n) human growth hormone,(o) insulin-like growth factor, (p) a P-38 protein kinase inhibitor, (q)bone morphogenic protein, (r) an inhibitor of BMP antagonism, (s) aprostaglandin derivative, (t) vitamin D or vitamin D derivative, (u)vitamin K or vitamin K derivative, (v) ipriflavone, (w) fluoride salts,and (x) dietary calcium supplement.
 24. A compound selected from: (1)N-(3-biphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(2)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(3)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(4)N-(3-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(5)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(6)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(7)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(8)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(9)N-(2-methyl-4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(10)N-(4-methoxy-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(11)N-(4-chloro-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(12)N-(2,4-dimethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(13)N-(3-bromo-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(14)N-(2,2,2-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(15)N-(2-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(16)N-(5-methyl-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(17)N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(18)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(19)N-(4-bromo-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(20)N-(4-chloro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(21)N-(2,4-dichlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(22)N-(3-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(23)N-(4-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(24)N-(5-fluoro-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(25)N-(5-chloro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(26)N-(2-phenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(27)N-(1-(3-phenylpropyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(28)N-(3-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(29)N-(2-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(30)N-(2-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(31)N-(3-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(32)N-(3-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(33)N-(4-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(34)N-(3-methoxybenzyl)-3-oxo-4-methyl4-aza-5α-androst-1-ene-17β-carboxamide,(35)N-(2-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(36)N-(cyclohexylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(37)N-(3-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(38)N-(2-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(39)N-(3-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(40)N-(4-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(41)N-(3-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(42)N-(3-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(43)N-(4-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(44)N-(2-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(45)N-(4-methoxylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(46)N-((R)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(47)N-((S)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(48)N-(3-(1-pyrrolidin-2-one)-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(49)N-(2-furanylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(50)N-(1-naphthylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(51)N-(2-(4-imidazoylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(52)N-(2-(3-indolylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(53)N-(5-indolyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(54)N-((1,2-methylenedioxy)-4-benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(55)N-(1,2-diphenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(56)N-(2-(1-hydroxy-1-phenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(57)N-(2-(2-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(58)N-(3-(1-imidazolyl)-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(59)N-(2-(2-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(60)N-(2-methoxyethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(61)N-(4-fluoro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(62)N-(2,4-difluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(63)N-(4-fluoro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(64)N-(4-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(65)N-(2-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(66)N-(3-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(67)N-(3,4-difluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(68)N-(4-dimethylaminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(69)N-(2-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(70)N-(2-benzamidazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(71)N-(1-(4-phenylbutyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(72)N-(3,5-dimethoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(73)N-(2-(2-pyridinylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(74)N-(2-methyl-5-pyrazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(75)N-(2-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(76)N-(2-(2-thiophenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(77)N-(1-(1-naphthyl)-1(R)-ethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(78)N-(2-(3-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(79)N-(2-(2-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(80)N-(2-(4-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(81)N-(2-(4-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(82)N-(2-(3-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(83)N-(2-(3,4-methylenedioxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(84)N-(2-thiophenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(85)N-(2-(4-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(86)N-(2-aminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(87)N-(2-(4-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(88) N-((1S, 2R)2-hydroxy-1-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(89)N-(2-dimethylaminoethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(90) N-(phenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(91)N-(2-chlorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(92)N-(2-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(93)N-(2-trifluoromethoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(94)N-(2-methoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(95) N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(96)N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(97)N-(1,1,1-trifluoroethyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(98) N-(2-propyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(99)N-(2-biphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(100)N-(2-acetylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(101)N-(3-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(102)N-(2-pyridinyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(103)N-(3-pyridinyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(104)N-(2-methylsulfonylphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(105)N-(2-methylsulfoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androst-1-ene-17β-carboxamide,(106) N-(phenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(107)N-(2-chlorophenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(108)N-(2-trifluoromethylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(109)N-(3-methylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(110)N-(2-methylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(111)N-(2-cyanophenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(112)N-(2-benzoylphenyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(113)N-(1,1,1-trifluoroethyl)-3-oxo-4-allyl-4-aza-5α-androst-1-ene-17β-carboxamide,(114) N-(phenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,(115)N-(2-chlorophenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,(116)N-(2-trifluoromethylphenyl)-3-oxo-4-benzyl-4-aza-5α-androst-1-ene-17β-carboxamide,(117) N-(phenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,(118)N-(2-trifluoromethylphenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,(119)N-(2-chlorophenyl)-3-oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxamide,(120)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(121)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(122)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(123)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(124)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(125)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(126) N-(phenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(127)N-(2-methoxyphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(128) N-(2-propyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(129) N-(2-biphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(130) N-(benzyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(131)N-(2-fluorophenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(132)N-(1,1,1-trifluoroethyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(133)N-(4-trifluoromethylphenyl)-3-oxo-4-ethyl-4-aza-5α-androstane-17β-carboxamide,(134)N-(1,1,1-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(135) N-(phenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-171-carboxamide,(136)N-(2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(137)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(138)N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(139)N-(2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(140)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(141)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(142)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(143)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(144)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(145)N-(2-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(146)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(147)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(148)N-(phenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(149)N-(2-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(150)N-(2-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(151)N-(3-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(152)N-(3-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(153)N-(4-trifluoromethylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(154)N-(2-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(155)N-(4-chlorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(156)N-(3-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(157)N-(4-fluorophenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(158)N-(2-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(159)N-(3-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,(160)N-(4-methylphenyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,and (161)N-(1,1,1-trifluoroethyl)-3-oxo-4-cyclopropyl-4-aza-5α-androst-5-ene-17β-carboxamide,and pharmaceutically acceptable salts thereof.
 25. The compoundaccording to claim 23, selected from: (1)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(2)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(3)N-(3-chlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(4)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(5)N-(4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(6)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(7)N-(4-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(8)N-(2-methyl-4-trifluoromethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(9)N-(4-methoxy-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(10)(N-(4-chloro-3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(11)(N-(2,4-dimethoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(12)(N-(3-bromo-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(13)(N-(2,2,2-trifluoroethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(14)(N-(2-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(15)(N-(5-methyl-2-pyridinyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(16)(N-(4-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(17)(N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(18)(N-(4-bromo-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(19)(N-(4-chloro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(20)(N-(2,4-dichlorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(21)(N-(3-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(22)(N-(4-cyanophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(23)(N-(5-chloro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(24)(N-(2-phenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(25)(N-(1-(3-phenylpropyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(26)(N-(2-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(27)(N-(2-biphenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(28)(N-(3-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(29)(N-(4-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(30)(N-(3-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(31)(N-(2-methoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(32)(N-(cyclohexylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(33)(N-(3-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(34)(N-(2-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(35)(N-(3-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(36)(N-(4-methylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(37)(N-(3-trifluoromethylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(38)N-(3-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(39)N-(4-fluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(40)N-(2-chlorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(41)N-(4-methoxylbenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(42)N-((R)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(43)N-((S)-2-phenyl-1-propyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(44)N-(2-furanylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(45)N-(1-naphthylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(46)N-(2-(3-indolylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(47)N-(5-indolyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(48)N-((1,2-methylenedioxy)-4-benzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(49)N-(1,2-diphenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(50)N-(2-(2-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(51)N-(2-(2-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(52)N-(4-fluoro-2-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(53)N-(2,4-difluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(54)N-(4-fluoro-2-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(55)N-(2-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(56)N-(3-phenoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(57)N-(3,4-difluorobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(58)N-(4-dimethylaminobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(59)N-(2-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(60)N-(2-benzamidazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(61)N-(3,5-dimethoxybenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(62)N-(2-(2-pyridinylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(63)N-(2-methyl-5-pyrazolemethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(64)N-(2-pyridinylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(65)N-(2-(2-thiophenylethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(66)N-(2-(3-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(67)N-(2-(2-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(68)N-(2-(4-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(69)N-(2-(4-nitrobenzyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(70)N-(2-(3-fluorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(71)N-(2-(3,4-methylenedioxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst1-ene-17β-carboxamide, (72)N-(2-thiophenylmethyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(73)N-(2-(4-methoxyphenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(74)N-(2-(2-aminobenzyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(75)N-(2-(4-chlorophenylethyl))-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(76) N-((1S, 2R)2-hydroxy-1-indanyl)-3-oxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide,(77)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(78)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(79)N-(4-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(80)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxamide,(81)N-(3-trifluoromethylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(82)N-(3-methylphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(83)N-(2-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(84)N-(3-fluorophenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(85)N-(3-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,(86)N-(4-methoxyphenyl)-3-oxo-4-methyl-4-aza-5α-androst-5-ene-17β-carboxamide,and pharmaceutically acceptable salts thereof.
 26. A compositioncomprising a compound according to claim 23 and a pharmaceuticallyacceptable carrier.
 27. A composition comprising a compound according toclaim 24 and a pharmaceutically acceptable carrier.
 28. The use of acompound of structural formula I

wherein: “a” and “b” are independently selected from a single bond and adouble bond; R¹ is selected from: (1) C₁₋₃ alkyl, (2) C₂₋₃ alkenyl, (3)C₃₋₆ cycloalkyl, (4) C₁₋₃ alkyl wherein one or more of the hydrogenatoms has been replaced with a fluorine atom, (5) aryl, and (6)aryl-C₁₋₃ alkyl; R² is selected from: (1) aryl, either unsubstituted orsubstituted with one to three substituents selected from: (a) halogen,(b) aryl, (c) C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈cycloheteroalkyl, (f) aryl C₁₋₆alkyl, (g) amino C₀₋₆alkyl, (h) C₁₋₆alkylamino C₀₋₆alkyl, (i) (C₁₋₆ alkyl)₂amino C₀₋₆alkyl, aryl C₀₋₆alkylamino C₀₋₆alkyl, (k) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆alkylthio, (m) aryl C₀₋₆alkylthio, (n) C₁₋₆ alkylsulfinyl, (o) arylC₀₋₆alkylsulfinyl, (p) C₁₋₆ alkylsulfonyl, (q) aryl C₀₋₆alkylsulfonyl,(r) C₁₋₆ alkoxy C₀₋₆alkyl, (s) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (t)hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (v) arylC₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonyl C₁₋₆ alkyloxy, (x)hydroxy C₀₋₆alkyl, (y) cyano, (z) nitro, (aa) perfluoroC₁₋₄alkyl, (bb)perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆ alkylcarbonyloxy, (ee) arylC₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆ carbonylamino, (gg) aryl C₀₋₆alkylcarbonylamino, (hh) C₁₋₆ alkylsulfonylamino, (ii) arylC₀₋₆alkylsulfonylamino, (j) C₁₋₆ alkoxycarbonylamino, (kk) aryl C₀₋₆alkoxycarbonylamino, (ll) C₁₋₆alkylaminocarbonylamino, (mm) arylC₀₋₆alkylaminocarbonylamino, (nn) (C₁₋₆alkyl)₂ aminocarbonylamino, (oo)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (pp) (C₁₋₆alkyl)₂aminocarbonyloxy, (qq) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, (rr)C₀₋₆alkylcarbonyl C₀₋₆alkyl, and (ss) aryl C₀₋₆alkylcarbonyl C₀₋₆alkyl;(2) C₁₋₈ alkyl, unsubstituted or substituted with one to threesubstituents independently selected from: (a) halogen, (b) aryl, (c)C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) amino,(g) C₁₋₆ alkylamino, (h) (C₁₋₆ alkyl)₂amino, (i) aryl C₀₋₆ alkylamino,(j) (aryl C₀₋₆ alkyl)₂amino, (k) C₁₋₆ alkylthio, (l) aryl C₀₋₆alkylthio,(m) C₁₋₆ alkylsulfinyl, (n) aryl C₀₋₆alkylsulfinyl, (o) C₁₋₆alkylsulfonyl, (p) aryl C₀₋₆alkylsulfonyl, (q) C₁₋₆ alkoxy, (r) arylC₀₋₆ alkoxy, (s) hydroxycarbonyl, (t) C₁₋₆ alkoxycarbonyl, (u) aryl C₀₋₆alkoxycarbonyl, (v) hydroxycarbonyl C₁₋₆ alkyloxy, (w) hydroxy, (x)cyano, (y) nitro, (z) perfluoroC₁₋₄alkyl, (aa) perfluoroC₁₋₄alkoxy, (bb)oxo, (cc) C₁₋₆ alkylcarbonyloxy, (dd) aryl C₀₋₆alkylcarbonyloxy, (ee)alkyl C₁₋₆ carbonylamino, (ff) aryl C₀₋₆ alkylcarbonylamino, (gg) C₁₋₆alkylsulfonylamino, (hh) aryl C₀₋₆alkylsulfonylamino, (ii) C₁₋₆alkoxycarbonylamino, (jj) aryl C₀₋₆ alkoxycarbonylamino, (kk)C₁₋₆alkylaminocarbonylamino, (ll) aryl C₀₋₆alkylaminocarbonylamino, (mm)(C₁₋₆alkyl)₂ aminocarbonylamino, (nn) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy, (pp) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (qq) spiro-C₃₋₈cycloalkyl; (3)perfluoroC₁₋₈ alkyl, (4) C₂₋₈ alkenyl, unsubstituted or substituted withone to three substituents independently selected from: (a) halogen, (b)aryl, (c) C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl,(f) amino, (g) C₁₋₆ alkylamino, (h) (C₁₋₆ alkyl)₂amino, (i) aryl C₀₋₆alkylamino, (j) (aryl C₀₋₆ alkyl)₂amino, (k) C₁₋₆ alkylthio, (l) arylC₀₋₆alkylthio, (m) C₁₋₆ alkylsulfinyl, (n) aryl C₀₋₆alkylsulfinyl, (o)C₁₋₆ alkylsulfonyl, (p) aryl C₀₋₆alkylsulfonyl, (q) C₁₋₆ alkoxy, (r)aryl C₀₋₆ alkoxy, (s) hydroxycarbonyl, (t) C₁₋₆ alkoxycarbonyl, (u) arylC₀₋₆ alkoxycarbonyl, (v) hydroxycarbonyl C₁₋₆ alkyloxy, (w) hydroxy, (x)cyano, (y) nitro, (z) perfluoroC₁₋₄alkyl, (aa) perfluoroC₁₋₄alkoxy, (bb)oxo, (cc) C₁₋₆ alkylcarbonyloxy, (dd) aryl C₀₋₆alkylcarbonyloxy, (ee)alkyl C₁₋₆ carbonylamino, (ff) aryl C₀₋₆ alkylcarbonylamino, (gg) C₁₋₆alkylsulfonylamino, (hh) aryl C₀₋₆alkylsulfonylamino, (ii) C₁₋₆alkoxycarbonylamino, (jj) aryl C₀₋₆ alkoxycarbonylamino, (kk)C₁₋₆alkylaminocarbonylamino, (ll) aryl C₀₋₆alkylaminocarbonylamino, (mm)(C₁₋₆alkyl)₂ aminocarbonylamino, (nn) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy, (pp) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (qq) spiro-C₃₋₈cycloalkyl; (5) C₃₋₈cycloalkyl, either unsubstituted or substituted with one to 3substituents selected from: (a) halogen, (b) aryl, (c) C₁₋₈ alkyl, (d)C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) aryl C₁₋₆alkyl, (g)amino C₀₋₆alkyl, (h) C₁₋₆ alkylamino C₀₋₆alkyl, (i) (C₁₋₆ alkyl)₂aminoC₀₋₆alkyl, (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (k) (aryl C₀₋₆alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆ alkylthio, (m) aryl C₀₋₆alkylthio, (n)C₁₋₆ alkylsulfinyl, (o) aryl C₀₋₆alkylsulfinyl,. (p) C₁₋₆ alkylsulfonyl,(q) aryl C₀₋₆alkylsulfonyl, (r) C₁₋₆ alkoxy C₀₋₆alkyl, (s) aryl C₀₋₆alkoxy C₀₋₆alkyl, (t) hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonylC₀₋₆alkyl, (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonylC₁₋₆ alkyloxy, (x) hydroxy C₀₋₆alkyl, (y) cyano, (z) nitro, (aa)perfluoroC₁₋₄alkyl, (bb) perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆alkylcarbonyloxy, (ee) aryl C₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆carbonylamino, (gg) aryl C₀₋₆ alkylcarbonylamino, (hh) C₁₋₆alkylsulfonylamino, (ii) aryl C₀₋₆alkylsulfonylamino, (jj) C₁₋₆alkoxycarbonylamino, (kk) aryl C₀₋₆ alkoxycarbonylamino, (ll)C₁₋₆alkylaminocarbonylamino, (mm) aryl C₀₋₆alkylaminocarbonylamino, (nn)(C₁₋₆alkyl)₂ aminocarbonylamino, (oo) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (pp) (C₁₋₆alkyl)₂ aminocarbonyloxy, (qq) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, (rr) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and (ss)spiro-C₃₋₈cycloalkyl; (6) cycloheteroalkyl, unsubstituted or substitutedwith one to three substituents selected from: (a) halogen, (b) aryl, (c)C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) arylC₁₋₆alkyl, (g) amino C₀₋₆alkyl, (h) C₁₋₆ alkylamino C₀₋₆alkyl, (i) (C₁₋₆alkyl)₂amino C₀₋₆alkyl, (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (k) (arylC₀₋₆ alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆ alkylthio, (m) aryl C₀₋₆alkylthio,(n) C₁₋₆ alkylsulfinyl, (o) aryl C₀₋₆alkylsulfinyl, (p) C₁₋₆alkylsulfonyl, (q) aryl C₀₋₆alkylsulfonyl, (r) C₁₋₆ alkoxy C₀₋₆alkyl,(s) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (t) hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆alkoxycarbonyl C₀₋₆alkyl, (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w)hydroxycarbonyl C₁₋₆ alkyloxy, (x) hydroxy C₀₋₆alkyl, (y) cyano, (z)nitro, (aa) perfluoroC₁₋₄alkyl, (bb) perfluoroC₁₋₄alkoxy, (cc) oxo, (dd)C₁₋₆ alkylcarbonyloxy, (ee) aryl C₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆carbonylamino, (gg) aryl C₀₋₆ alkylcarbonylamino, (hh) C₁₋₆alkylsulfonylamino, (ii) aryl C₀₋₆alkylsulfonylamino, (j) C₁₋₆alkoxycarbonylamino, (kk) aryl C₀₋₆ alkoxycarbonylamino, (ll)C₁₋₆alkylaminocarbonylamino, (mm) aryl C₀₋₆alkylaminocarbonylamino, (nn)(C₁₋₆alkyl)₂ aminocarbonylamino, (oo) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (pp) (C₁₋₆alkyl)₂ aminocarbonyloxy, (qq) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (rr) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and(ss) spiro C₃₋₈cycloalkyl provided that any heteroatom substituent isbonded to a carbon atom in the cycloheteroalkyl ring; R³ is selectedfrom H and C₁₋₈ alkyl, or R² and R³, together with the nitrogen atom towhich they are attached, form a 5- to 7-membered heterocyclic ring,optionally containing one or two additional heteroatoms selected from N,S, and O, optionally having one or more degrees of unsaturation,optionally fused to a 6-membered heteroaromatic or aromatic ring, eitherunsubstituted or substituted with one to three substituents selectedfrom: (1) halogen, (2) aryl, (3) C₁₋₈ alkyl, (4) C₃₋₈ cycloalkyl, (5)C₃₋₈ cycloheteroalkyl, (6) aryl C₁₋₆alkyl, (7) amino C₀₋₆alkyl, (8) C₁₋₆alkylamino C₀₋₆alkyl, (9) (C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (10) aryl C₀₋₆alkylamino C₀₋₆alkyl, (11) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (12) C₁₋₆alkylthio, (13) aryl C₀₋₆alkylthio, (14) C₁₋₆ alkylsulfinyl, (15) arylC₀₋₆alkylsulfinyl, (16) C₁₋₆ alkylsulfonyl, (17) aryl C₀₋₆alkylsulfonyl,(18) C₁₋₆ alkoxy C₀₋₆alkyl, (19) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (20)hydroxycarbonyl C₀₋₆alkyl, (21) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (22) arylC₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (23) hydroxycarbonyl C₁₋₆ alkyloxy, (24)hydroxy C₀₋₆alkyl, (25) cyano, (26) nitro, (27) perfluoroC₁₋₄alkyl, (28)perfluoroC₁₋₄alkoxy, (29) oxo, (30) C₁₋₆ alkylcarbonyloxy, (31) arylC₀₋₆alkylcarbonyloxy, (32) C₁₋₆ alkyl carbonylamino, (33) aryl C₀₋₆alkylcarbonylamino, (34) C₁₋₆ alkylsulfonylamino, (35) arylC₀₋₆alkylsulfonylamino, (36) C₁₋₆ alkoxycarbonylamino, (37) aryl C₀₋₆alkoxycarbonylamino, (38) C₁₋₆alkylaminocarbonylamino, (39) arylC₀₋₆alkylaminocarbonylamino, (40) (C₁₋₆alkyl)₂ aminocarbonylamino, (41)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (42) (C₁₋₆alkyl)₂aminocarbonyloxy, (43) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, and (44)spiro-C₃₋₈cycloalkyl provided that any heteroatom substituent is bondedto a carbon atom in the heterocyclic ring; R⁴ and R⁵ are eachindependently selected from (1) hydrogen, (2) halogen, (3) aryl, (4)C₁₋₈ alkyl, (5) C₃₋₈ cycloalkyl, (6) C₃₋₈ cycloheteroalkyl, (7) arylC₁₋₆alkyl, (8) amino C₀₋₆alkyl, (9) C₁₋₆ alkylamino C₀₋₆alkyl, (10)(C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (11) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (12)(aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (13) C₁₋₆ alkylthio, (14) arylC₀₋₆alkylthio, (15) C₁₋₆ alkylsulfinyl, (16) aryl C₀₋₆alkylsulfinyl,(17) C₁₋₆ alkylsulfonyl, (18) aryl C₀₋₆alkylsulfonyl, (19) C₁₋₆ alkoxyC₀₋₆alkyl, (20) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (21) hydroxycarbonylC₀₋₆alkyl, (22) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (23) aryl C₀₋₆alkoxycarbonyl C₀₋₆alkyl, (24) hydroxycarbonyl C₁₋₆ alkyloxy, (25)hydroxy C₀₋₆alkyl, (26) cyano, (27) nitro, (28) perfluoroC₁₋₄alkyl, (29)perfluoroC₁₋₄alkoxy, (30) C₀₋₆alkylcarbonyl C₀₋₆alkyl, (31) C₁₋₆alkylcarbonyloxy, (32) aryl C₀₋₆alkylcarbonyloxy, (33) C₁₋₆ alkylcarbonylamino, (34) aryl C₀₋₆ alkylcarbonylamino, (35) C₁₋₆alkylsulfonylamino, (36) aryl C₀₋₆alkylsulfonylamino, (37) C₁₋₆alkoxycarbonylamino, (38) aryl C₀₋₆ alkoxycarbonylamino, (39)C₁₋₆alkylaminocarbonylamino, (40) aryl C₀₋₆alkylaminocarbonylamino, (41)(C₁₋₆alkyl)₂ aminocarbonylamino, (42) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (43) (C₁₋₆alkyl)₂ aminocarbonyloxy, and (44) (arylC₀₋₆alkyl)₂ aminocarbonyloxy; or, R⁴ and R⁵ together form an oxo groupor ═CH—R⁶ or a spiro C₃₋₇ cycloalkyl ring, unsubstituted or substitutedwith R⁶; R⁶ is selected from: (1) hydrogen, and (2) C₁₋₄ alkyl; or apharmaceutically acceptable salt thereof. for the preparation of amedicament useful for modulating the androgen receptor in a tissueselective manner in a patient in need of such modulation.
 29. The use ofa compound of structural formula I

wherein: “a” and “b” are independently selected from a single bond and adouble bond; R¹ is selected from: (1) C₁₋₃ alkyl, (2) C₂₋₃ alkenyl, (3)C₃₋₆ cycloalkyl, (4) C₁₋₃ alkyl wherein one or more of the hydrogenatoms has been replaced with a fluorine atom, (5) aryl, and (6)aryl-C₁₋₃ alkyl; R² is selected from: (1) aryl, either unsubstituted orsubstituted with one to three substituents selected from: (a) halogen,(b) aryl, (c) C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈cycloheteroalkyl, (f) aryl C₁₋₆alkyl, (g) amino C₀₋₆alkyl, (h) C₁₋₆alkylamino C₀₋₆alkyl, (i) (C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (j) aryl C₀₋₆alkylamino C₀₋₆alkyl, (k) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆alkylthio, (m) aryl C₀₋₆alkylthio, (n) C₁₋₆ alkylsulfinyl, (o) arylC₀₋₆alkylsulfinyl, (p) C₁₋₆ alkylsulfonyl, (q) aryl C₀₋₆alkylsulfonyl,(r) C₁₋₆ alkoxy C₀₋₆alkyl, (s) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (t)hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (v) arylC₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonyl C₁₋₆ alkyloxy, (x)hydroxy C₀₋₆alkyl, (y) cyano, (z) nitro, (aa) perfluoroC₁₋₄alkyl, (bb)perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆ alkylcarbonyloxy, (ee) arylC₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆ carbonylamino, (gg) aryl C₀₋₆alkylcarbonylamino, (hh) C₁₋₆ alkylsulfonylamino, (ii) arylC₀₋₆alkylsulfonylamino, (jj) C₁₋₆ alkoxycarbonylamino, (kk) aryl C₀₋₆alkoxycarbonylamino, (ll) C₁₋₆alkylaminocarbonylamino, (mm) arylC₀₋₆alkylaminocarbonylamino, (nn) (C₁₋₆alkyl)₂ aminocarbonylamino, (oo)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (pp) (C₁₋₆alkyl)₂aminocarbonyloxy, (qq) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, (rr)C₀₋₆alkylcarbonyl C₀₋₆alkyl, and (ss) aryl C₀₋₆alkylcarbonyl C₀₋₆alkyl;(2) C₁₋₈ alkyl, unsubstituted or substituted with one to threesubstituents independently selected from: (a) halogen, (b) aryl, (c)C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) amino,(g) C₁₋₆ alkylamino, (h) (C₁₋₆ alkyl)₂amino, (i) aryl C₀₋₆ alkylamino,(j) (aryl C₀₋₆ alkyl)₂amino, (k) C₁₋₆ alkylthio, (l) aryl C₀₋₆alkylthio,(m) C₁₋₆ alkylsulfinyl, (n) aryl C₀₋₆alkylsulfinyl, (o) C₁₋₆alkylsulfonyl, (p) aryl C₀₋₆alkylsulfonyl, (q) C₁₋₆ alkoxy, (r) arylC₀₋₆ alkoxy, (s) hydroxycarbonyl, (t) C₁₋₆ alkoxycarbonyl, (u) aryl C₀₋₆alkoxycarbonyl, (v) hydroxycarbonyl C₁₋₆ alkyloxy, (w) hydroxy, (x)cyano, (y) nitro, (z) perfluoroC₁₋₄alkyl, (aa) perfluoroC₁₋₄alkoxy, (bb)oxo, (cc) C₁₋₆ alkylcarbonyloxy, (dd) aryl C₀₋₆alkylcarbonyloxy, (ee)alkyl C₁₋₆ carbonylamino, (ff) aryl C₀₋₆ alkylcarbonylamino, (gg) C₁₋₆alkylsulfonylamino, (hh) aryl C₀₋₆alkylsulfonylamino, (ii) C₁₋₆alkoxycarbonylamino, (jj) aryl C₀₋₆ alkoxycarbonylamino, (kk)C₁₋₆alkylaminocarbonylamino, (ll) aryl C₀₋₆alkylaminocarbonylamino, (mm)(C₁₋₆alkyl)₂ aminocarbonylamino, (nn) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy, (pp) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (qq) spiro-C₃₋₈cycloalkyl; (3)perfluoroC₁₋₈ alkyl, (4) C₂₋₈ alkenyl, unsubstituted or substituted withone to three substituents independently selected from: (a) halogen, (b)aryl, (c) C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl,(f) amino, (g) C₁₋₆ alkylamino, (h) (C₁₋₆ alkyl)₂amino, (i) aryl C₀₋₆alkylamino, (j) (aryl C₀₋₆ alkyl)₂amino, (k) C₁₋₆ alkylthio, (l) arylC₀₋₆alkylthio, (m) C₁₋₆ alkylsulfinyl, (n) aryl C₀₋₆alkylsulfinyl, (o)C₁₋₆ alkylsulfonyl, (p) aryl C₀₋₆alkylsulfonyl, (q) C₁₋₆ alkoxy, (r)aryl C₀₋₆ alkoxy, (s) hydroxycarbonyl, (t) C₁₋₆ alkoxycarbonyl, (u) arylC₀₋₆ alkoxycarbonyl, (v) hydroxycarbonyl C₁₋₆ alkyloxy, (w) hydroxy, (x)cyano, (y) nitro, (z) perfluoroC₁₋₄alkyl, (aa) perfluoroC₁₋₄alkoxy, (bb)oxo, (cc) C₁₋₆ alkylcarbonyloxy, (dd) aryl C₀₋₆alkylcarbonyloxy, (ee)alkyl C₁₋₆ carbonylamino, (ff) aryl C₀₋₆ alkylcarbonylamino, (gg) C₁₋₆alkylsulfonylamino, (hh) aryl C₀₋₆alkylsulfonylamino, (ii) C₁₋₆alkoxycarbonylamino, (jj) aryl C₀₋₆ alkoxycarbonylamino, (kk)C₁₋₆alkylaminocarbonylamino, (ll) aryl C₀₋₆alkylaminocarbonylamino, (mm)(C₁₋₆alkyl)₂ aminocarbonylamino, (nn) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy, (pp) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (qq) spiro-C₃₋₈cycloalkyl; (5) C₃₋₈cycloalkyl, either unsubstituted or substituted with one to 3substituents selected from: (a) halogen, (b) aryl, (c) C₁₋₈ alkyl, (d)C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) aryl C₁₋₆alkyl, (g)amino C₀₋₆alkyl, (h) C₁₋₆ alkylamino C₀₋₆alkyl, (i) (C₁₋₆ alkyl)₂aminoC₀₋₆alkyl, (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (k) (aryl C₀₋₆alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆ alkylthio, (m) aryl C₀₋₆alkylthio, (n)C₁₋₆ alkylsulfinyl, (o) aryl C₀₋₆alkylsulfinyl, (p) C₁₋₆ alkylsulfonyl,(q) aryl C₀₋₆alkylsulfonyl, (r) C₁₋₆ alkoxy C₀₋₆alkyl, (s) aryl C₀₋₆alkoxy C₀₋₆alkyl, (t) hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonylC₀₋₆alkyl, (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonylC₁₋₆ alkyloxy, (x) hydroxy C₀₋₆alkyl, (y) cyano, (z) nitro, (aa)perfluoroC₁₋₄alkyl, (bb) perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆alkylcarbonyloxy, (ee) aryl C₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆carbonylamino, (gg) aryl C₀₋₆ alkylcarbonylamino, (hh) C₁₋₆alkylsulfonylamino, (ii) aryl C₀₋₆alkylsulfonylamino, (jj) C₁₋₆alkoxycarbonylamino, (kk) aryl C₀₋₆ alkoxycarbonylamino, (ll)C₁₋₆alkylaminocarbonylamino, (mm) aryl C₀₋₆alkylaminocarbonylamino, (nn)(C₁₋₆alkyl)₂ aminocarbonylamino, (oo) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (pp) (C₁₋₆alkyl)₂ aminocarbonyloxy, (qq) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, (rr) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and (ss)spiro-C₃₋₈cycloalkyl; (6) cycloheteroalkyl, unsubstituted or substitutedwith one to three substituents selected from: (a) halogen, (b) aryl, (c)C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) arylC₁₋₆alkyl, (g) amino C₀₋₆alkyl, (h) C₁₋₆ alkylamino C₀₋₆alkyl, (i) (C₁₋₆alkyl)₂amino C₀₋₆alkyl, (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (k) (arylC₀₋₆ alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆ alkylthio, (m) aryl C₀₋₆alkylthio,(n) C₁₋₆ alkylsulfinyl, (o) aryl C₀₋₆alkylsulfinyl, (p) C₁₋₆alkylsulfonyl, (q) aryl C₀₋₆alkylsulfonyl, (r) C₁₋₆ alkoxy C₀₋₆alkyl,(s) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (t) hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆alkoxycarbonyl C₀₋₆alkyl, (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w)hydroxycarbonyl C₁₋₆ alkyloxy, (x) hydroxy C₀₋₆alkyl, (y) cyano, (z)nitro, (aa) perfluoroC₁₋₄alkyl, (bb) perfluoroC₁₋₄alkoxy, (cc) oxo, (dd)C₁₋₆ alkylcarbonyloxy, (ee) aryl C₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆carbonylamino, (gg) aryl C₀₋₆ alkylcarbonylamino, (hh) C₁₋₆alkylsulfonylamino, (ii) aryl C₀₋₆alkylsulfonylamino, (jj) C₁₋₆alkoxycarbonylamino, (kk) aryl C₀₋₆ alkoxycarbonylamino, (ll)C₁₋₆alkylaminocarbonylamino, (mm) aryl C₀₋₆alkylaminocarbonylamino, (nn)(C₁₋₆alkyl)₂ aminocarbonylamino, (oo) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (pp) (C₁₋₆alkyl)₂ aminocarbonyloxy, (qq) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (rr) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and(ss) spiro C₃₋₈cycloalkyl provided that any heteroatom substituent isbonded to a carbon atom in the cycloheteroalkyl ring; R³ is selectedfrom H and C₁₋₈ alkyl, or R² and R³, together with the nitrogen atom towhich they are attached, form a 5- to 7-membered heterocyclic ring,optionally containing one or two additional heteroatoms selected from N,S, and O, optionally having one or more degrees of unsaturation,optionally fused to a 6-membered heteroaromatic or aromatic ring, eitherunsubstituted or substituted with one to three substituents selectedfrom: (1) halogen, (2) aryl, (3) C₁₋₈ alkyl, (4) C₃₋₈ cycloalkyl, (5)C₃₋₈ cycloheteroalkyl, (6) aryl C₁₋₆alkyl, (7) amino C₀₋₆alkyl, (8) C₁₋₆alkylamino C₀₋₆alkyl, (9) (C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (10) aryl C₀₋₆alkylamino C₀₋₆alkyl, (11) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (12) C₁₋₆alkylthio, (13) aryl C₀₋₆alkylthio, (14) C₁₋₆ alkylsulfinyl, (15) arylC₀₋₆alkylsulfinyl, (16) C₁₋₆ alkylsulfonyl, (17) aryl C₀₋₆alkylsulfonyl,(18) C₁₋₆ alkoxy C₀₋₆alkyl, (19) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (20)hydroxycarbonyl C₀₋₆alkyl, (21) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (22) arylC₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (23) hydroxycarbonyl C₁₋₆ alkyloxy, (24)hydroxy C₀₋₆alkyl, (25) cyano, (26) nitro, (27) perfluoroC₁₋₄alkyl, (28)perfluoroC₁₋₄alkoxy, (29) oxo, (30) C₁₋₆ alkylcarbonyloxy, (31) arylC₀₋₆alkylcarbonyloxy, (32) C₁₋₆ alkyl carbonylamino, (33) aryl C₀₋₆alkylcarbonylamino, (34) C₁₋₆ alkylsulfonylamino, (35) arylC₀₋₆alkylsulfonylamino, (36) C₁₋₆ alkoxycarbonylamino, (37) aryl C₀₋₆alkoxycarbonylamino, (38) C₁₋₆alkylaminocarbonylamino, (39) arylC₀₋₆alkylaminocarbonylamino, (40) (C₁₋₆alkyl)₂ aminocarbonylamino, (41)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (42) (C₁₋₆alkyl)₂aminocarbonyloxy, (43) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, and (44)spiro-C₃₋₈cycloalkyl provided that any heteroatom substituent is bondedto a carbon atom in the heterocyclic ring; R⁴ and R⁵ are eachindependently selected from (1) hydrogen, (2) halogen, (3) aryl, (4)C₁₋₈ alkyl, (5) C₃₋₈ cycloalkyl, (6) C₃₋₈ cycloheteroalkyl, (7) arylC₁₋₆alkyl, (8) amino C₀₋₆alkyl, (9) C₁₋₆ alkylamino C₀₋₆alkyl, (10)(C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (11) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (12)(aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (13) C₁₋₆ alkylthio, (14) arylC₀₋₆alkylthio, (15) C₁₋₆ alkylsulfinyl, (16) aryl C₀₋₆alkylsulfinyl,(17) C₁₋₆ alkylsulfonyl, (18) aryl C₀₋₆alkylsulfonyl, (19) C₁₋₆ alkoxyC₀₋₆alkyl, (20) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (21) hydroxycarbonylC₀₋₆alkyl, (22) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (23) aryl C₀₋₆alkoxycarbonyl C₀₋₆alkyl, (24) hydroxycarbonyl C₁₋₆ alkyloxy, (25)hydroxy C₀₋₆alkyl, (26) cyano, (27) nitro, (28) perfluoroC₁₋₄alkyl, (29)perfluoroC₁₋₄alkoxy, (30) C₀₋₆alkylcarbonyl C₀₋₆alkyl, (31) C₁₋₆alkylcarbonyloxy, (32) aryl C₀₋₆alkylcarbonyloxy, (33) C₁₋₆ alkylcarbonylamino, (34) aryl C₀₋₆ alkylcarbonylamino, (35) C₁₋₆alkylsulfonylamino, (36) aryl C₀₋₆alkylsulfonylamino, (37) C₁₋₆alkoxycarbonylamino, (38) aryl C₀₋₆ alkoxycarbonylamino, (39)C₁₋₆alkylaminocarbonylamino, (40) aryl C₀₋₆alkylaminocarbonylamino, (41)(C₁₋₆alkyl)₂ aminocarbonylamino, (42) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (43) (C₁₋₆alkyl)₂ aminocarbonyloxy, and (44) (arylC₀₋₆alkyl)₂ aminocarbonyloxy; or, R⁴ and R⁵ together form an oxo groupor ═CH—R⁶ or a spiro C₃₋₇ cycloalkyl ring, unsubstituted or substitutedwith R⁶; R⁶ is selected from: (1) hydrogen, and (2) C₁₋₄ alkyl; or apharmaceutically acceptable salt thereof. for the preparation of amedicament useful for agonizing the androgen receptor in a patient inneed thereof.
 30. The use of a compound of structural formula I

wherein: “a” and “b” are independently selected from a single bond and adouble bond; R¹ is selected from: (1) C₁₋₃ alkyl, (2) C₂₋₃ alkenyl, (3)C₃₋₆ cycloalkyl, (4) C₁₋₃ alkyl wherein one or more of the hydrogenatoms has been replaced with a fluorine atom, (5) aryl, and (6)aryl-C₁₋₃ alkyl; R² is selected from: (1) aryl, either unsubstituted orsubstituted with one to three substituents selected from: (a) halogen,(b) aryl, (c) C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈cycloheteroalkyl, (f) aryl C₁₋₆alkyl, (g) amino C₀₋₆alkyl, (h) C₁₋₆alkylamino C₀₋₆alkyl, (i) (C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (j) aryl C₀₋₆alkylamino C₀₋₆alkyl, (k) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆alkylthio, (m) aryl C₀₋₆alkylthio, (n) C₁₋₆ alkylsulfinyl, (o) arylC₀₋₆alkylsulfinyl, (p) C₁₋₆ alkylsulfonyl, (q) aryl C₀₋₆alkylsulfonyl,(r) C₁₋₆ alkoxy C₀₋₆alkyl, (s) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (t)hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (v) arylC₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonyl C₁₋₆ alkyloxy, (x)hydroxy C₀₋₆alkyl, (y) cyano, (z) nitro, (aa) perfluoroC₁₋₄alkyl, (bb)perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆ alkylcarbonyloxy, (ee) arylC₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆ carbonylamino, (gg) aryl C₀₋₆alkylcarbonylamino, (hh) C₁₋₆ alkylsulfonylamino, (ii) arylC₀₋₆alkylsulfonylamino, (jj) C₁₋₆ alkoxycarbonylamino, (kk) aryl C₀₋₆alkoxycarbonylamino, (ll) C₁₋₆alkylaminocarbonylamino, (mm) arylC₀₋₆alkylaminocarbonylamino, (nn) (C₁₋₆alkyl)₂ aminocarbonylamino, (oo)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (pp) (C₁₋₆alkyl)₂aminocarbonyloxy, (qq) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, (rr)C₀₋₆alkylcarbonyl C₀₋₆alkyl, and (ss) aryl C₀₋₆alkylcarbonyl C₀₋₆alkyl;(2) C₁₋₈ alkyl, unsubstituted or substituted with one to threesubstituents independently selected from: (a) halogen, (b) aryl, (c)C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) amino,(g) C₁₋₆ alkylamino, (h) (C₁₋₆ alkyl)₂amino, (i) aryl C₀₋₆ alkylamino,(j) (aryl C₀₋₆ alkyl)₂amino, (k) C₁₋₆ alkylthio, (l) aryl C₀₋₆alkylthio,(m) C₁₋₆ alkylsulfinyl, (n) aryl C₀₋₆alkylsulfinyl, (o) C₁₋₆alkylsulfonyl, (p) aryl C₀₋₆alkylsulfonyl, (q) C₁₋₆ alkoxy, (r) arylC₀₋₆ alkoxy, (s) hydroxycarbonyl, (t) C₁₋₆ alkoxycarbonyl, (u) aryl C₀₋₆alkoxycarbonyl, (v) hydroxycarbonyl C₁₋₆ alkyloxy, (w) hydroxy, (x)cyano, (y) nitro, (z) perfluoroC₁₋₄alkyl, (aa) perfluoroC₁₋₄alkoxy, (bb)oxo, (cc) C₁₋₆ alkylcarbonyloxy, (dd) aryl C₀₋₆alkylcarbonyloxy, (ee)alkyl C₁₋₆ carbonylamino, (ff) aryl C₀₋₆ alkylcarbonylamino, (gg) C₁₋₆alkylsulfonylamino, (hh) aryl C₀₋₆alkylsulfonylamino, (ii) C₁₋₆alkoxycarbonylamino, (jj) aryl C₀₋₆ alkoxycarbonylamino, (kk)C₁₋₆alkylaminocarbonylamino, (ll) aryl C₀₋₆alkylaminocarbonylamino, (mm)(C₁₋₆alkyl)₂ aminocarbonylamino, (nn) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy, (pp) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (qq) spiro-C₃₋₈cycloalkyl; (3)perfluoroC₁₋₈ alkyl, (4) C₂₋₈ alkenyl, unsubstituted or substituted withone to three substituents independently selected from: (a) halogen, (b)aryl, (c) C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl,(f) amino, (g) C₁₋₆ alkylamino, (h) (C₁₋₆ alkyl)₂amino, (i) aryl C₀₋₆alkylamino, (j) (aryl C₀₋₆ alkyl)₂amino, (k) C₁₋₆ alkylthio, (l) arylC₀₋₆alkylthio, (m) C₁₋₆ alkylsulfinyl, (n) aryl C₀₋₆alkylsulfinyl, (o)C₁₋₆ alkylsulfonyl, (p) aryl C₀₋₆alkylsulfonyl, (q) C₁₋₆ alkoxy, (r)aryl C₀₋₆ alkoxy, (s) hydroxycarbonyl, (t) C₁₋₆ alkoxycarbonyl, (u) arylC₀₋₆ alkoxycarbonyl, (v) hydroxycarbonyl C₁₋₆ alkyloxy, (w) hydroxy, (x)cyano, (y) nitro, (z) perfluoroC₁₋₄alkyl, (aa) perfluoroC₁₋₄alkoxy, (bb)oxo, (cc) C₁₋₆ alkylcarbonyloxy, (dd) aryl C₀₋₆alkylcarbonyloxy, (ee)alkyl C₁₋₆ carbonylamino, (ff) aryl C₀₋₆ alkylcarbonylamino, (gg) C₁₋₆alkylsulfonylamino, (hh) aryl C₀₋₆alkylsulfonylamino, (ii) C₁₋₆alkoxycarbonylamino, (jj) aryl C₀₋₆ alkoxycarbonylamino, (kk)C₁₋₆alkylaminocarbonylamino, (ll) aryl C₀₋₆alkylaminocarbonylamino, (mm)(C₁₋₆alkyl)₂ aminocarbonylamino, (nn) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (oo) (C₁₋₆alkyl)₂ aminocarbonyloxy, (pp) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (qq) spiro-C₃₋₈cycloalkyl; (5) C₃₋₈cycloalkyl, either unsubstituted or substituted with one to 3substituents selected from: (a) halogen, (b) aryl, (c) C₁₋₈ alkyl, (d)C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) aryl C₁₋₆alkyl, (g)amino C₀₋₆alkyl, (h) C₁₋₆ alkylamino C₀₋₆alkyl, (i) (C₁₋₆ alkyl)₂aminoC₀₋₆alkyl, (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (k) (aryl C₀₋₆alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆ alkylthio, (m) aryl C₀₋₆alkylthio, (n)C₁₋₆ alkylsulfinyl, (o) aryl C₀₋₆alkylsulfinyl, (p) C₁₋₆ alkylsulfonyl,(q) aryl C₀₋₆alkylsulfonyl, (r) C₁₋₆ alkoxy C₀₋₆alkyl, (s) aryl C₀₋₆alkoxy C₀₋₆alkyl, (t) hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆ alkoxycarbonylC₀₋₆alkyl, (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w) hydroxycarbonylC₁₋₆ alkyloxy, (x) hydroxy C₀₋₆alkyl, (y) cyano, (z) nitro, (aa)perfluoroC₁₋₄alkyl, (bb) perfluoroC₁₋₄alkoxy, (cc) oxo, (dd) C₁₋₆alkylcarbonyloxy, (ee) aryl C₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆carbonylamino, (gg) aryl C₀₋₆ alkylcarbonylamino, (hh) C₁₋₆alkylsulfonylamino, (ii) aryl C₀₋₆alkylsulfonylamino, (jj) C₁₋₆alkoxycarbonylamino, (kk) aryl C₀₋₆ alkoxycarbonylamino, (ll)C₁₋₆alkylaminocarbonylamino, (mm) aryl C₀₋₆alkylaminocarbonylamino, (nn)(C₁₋₆alkyl)₂ aminocarbonylamino, (oo) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (pp) (C₁₋₆alkyl)₂ aminocarbonyloxy, (qq) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, (rr) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and (ss)spiro-C₃₋₈cycloalkyl; (6) cycloheteroalkyl, unsubstituted or substitutedwith one to three substituents selected from: (a) halogen, (b) aryl, (c)C₁₋₈ alkyl, (d) C₃₋₈ cycloalkyl, (e) C₃₋₈ cycloheteroalkyl, (f) arylC₁₋₆alkyl, (g) amino C₀₋₆alkyl, (h) C₁₋₆ alkylamino C₀₋₆alkyl, (i) (C₁₋₆alkyl)₂amino C₀₋₆alkyl, (j) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (k) (arylC₀₋₆ alkyl)₂amino C₀₋₆alkyl, (l) C₁₋₆ alkylthio, (m) aryl C₀₋₆alkylthio,(n) C₁₋₆ alkylsulfinyl, (o) aryl C₀₋₆alkylsulfinyl, (p) C₁₋₆alkylsulfonyl, (q) aryl C₀₋₆alkylsulfonyl, (r) C₁₋₆ alkoxy C₀₋₆alkyl,(s) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (t) hydroxycarbonyl C₀₋₆alkyl, (u) C₁₋₆alkoxycarbonyl C₀₋₆alkyl, (v) aryl C₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (w)hydroxycarbonyl C₁₋₆ alkyloxy, (x) hydroxy C₀₋₆alkyl, (y) cyano, (z)nitro, (aa) perfluoroC₁₋₄alkyl, (bb) perfluoroC₁₋₄alkoxy, (cc) oxo, (dd)C₁₋₆ alkylcarbonyloxy, (ee) aryl C₀₋₆alkylcarbonyloxy, (ff) alkyl C₁₋₆carbonylamino, (gg) aryl C₀₋₆ alkylcarbonylamino, (hh) C₁₋₆alkylsulfonylamino, (ii) aryl C₀₋₆alkylsulfonylamino, (jj) C₁₋₆alkoxycarbonylamino, (kk) aryl C₀₋₆ alkoxycarbonylamino, (ll)C₁₋₆alkylaminocarbonylamino, (mm) aryl C₀₋₆alkylaminocarbonylamino, (nn)(C₁₋₆alkyl)₂ aminocarbonylamino, (oo) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (pp) (C₁₋₆alkyl)₂ aminocarbonyloxy, (qq) (arylC₀₋₆alkyl)₂ aminocarbonyloxy, and (rr) C₀₋₆alkylcarbonyl C₀₋₆alkyl, and(ss) spiro C₃₋₈cycloalkyl provided that any heteroatom substituent isbonded to a carbon atom in the cycloheteroalkyl ring; R³ is selectedfrom H and C₁₋₈ alkyl, or R² and R³, together with the nitrogen atom towhich they are attached, form a 5- to 7-membered heterocyclic ring,optionally containing one or two additional heteroatoms selected from N,S, and O, optionally having one or more degrees of unsaturation,optionally fused to a 6-membered heteroaromatic or aromatic ring, eitherunsubstituted or substituted with one to three substituents selectedfrom: (1) halogen, (2) aryl, (3) C₁₋₈ alkyl, (4) C₃₋₈ cycloalkyl, (5)C₃₋₈ cycloheteroalkyl, (6) aryl C₁₋₆alkyl, (7) amino C₀₋₆alkyl, (8) C₁₋₆alkylamino C₀₋₆alkyl, (9) (C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (10) aryl C₀₋₆alkylamino C₀₋₆alkyl, (11) (aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (12) C₁₋₆alkylthio, (13) aryl C₀₋₆alkylthio, (14) C₁₋₆ alkylsulfinyl, (15) arylC₀₋₆alkylsulfinyl, (16) C₁₋₆ alkylsulfonyl, (17) aryl C₀₋₆alkylsulfonyl,(18) C₁₋₆ alkoxy C₀₋₆alkyl, (19) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (20)hydroxycarbonyl C₀₋₆alkyl, (21) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (22) arylC₀₋₆ alkoxycarbonyl C₀₋₆alkyl, (23) hydroxycarbonyl C₁₋₆ alkyloxy, (24)hydroxy C₀₋₆alkyl, (25) cyano, (26) nitro, (27) perfluoroC₁₋₄alkyl, (28)perfluoroC₁₋₄alkoxy, (29) oxo, (30) C₁₋₆ alkylcarbonyloxy, (31) arylC₀₋₆alkylcarbonyloxy, (32) C₁₋₆ alkyl carbonylamino, (33) aryl C₀₋₆alkylcarbonylamino, (34) C₁₋₆ alkylsulfonylamino, (35) arylC₀₋₆alkylsulfonylamino, (36) C₁₋₆ alkoxycarbonylamino, (37) aryl C₀₋₆alkoxycarbonylamino, (38) C₁₋₆alkylaminocarbonylamino, (39) arylC₀₋₆alkylaminocarbonylamino, (40) (C₁₋₆alkyl)₂ aminocarbonylamino, (41)(aryl C₀₋₆alkyl)₂ aminocarbonylamino, (42) (C₁₋₆alkyl)₂aminocarbonyloxy, (43) (aryl C₀₋₆alkyl)₂ aminocarbonyloxy, and (44)spiro-C₃₋₈cycloalkyl provided that any heteroatom substituent is bondedto a carbon atom in the heterocyclic ring; R⁴ and R⁵ are eachindependently selected from (1) hydrogen, (2) halogen, (3) aryl, (4)C₁₋₈ alkyl, (5) C₃₋₈ cycloalkyl, (6) C₃₋₈ cycloheteroalkyl, (7) arylC₁₋₆alkyl, (8) amino C₀₋₆alkyl, (9) C₁₋₆ alkylamino C₀₋₆alkyl, (10)(C₁₋₆ alkyl)₂amino C₀₋₆alkyl, (11) aryl C₀₋₆ alkylamino C₀₋₆alkyl, (12)(aryl C₀₋₆ alkyl)₂amino C₀₋₆alkyl, (13) C₁₋₆ alkylthio, (14) arylC₀₋₆alkylthio, (15) C₁₋₆ alkylsulfinyl, (16) aryl C₀₋₆alkylsulfinyl,(17) C₁₋₆ alkylsulfonyl, (18) aryl C₀₋₆alkylsulfonyl, (19) C₁₋₆ alkoxyC₀₋₆alkyl, (20) aryl C₀₋₆ alkoxy C₀₋₆alkyl, (21) hydroxycarbonylC₀₋₆alkyl, (22) C₁₋₆ alkoxycarbonyl C₀₋₆alkyl, (23) aryl C₀₋₆alkoxycarbonyl C₀₋₆alkyl, (24) hydroxycarbonyl C₁₋₆ alkyloxy, (25)hydroxy C₀₋₆alkyl, (26) cyano, (27) nitro, (28) perfluoroC₁₋₄alkyl, (29)perfluoroC₁₋₄alkoxy, (30) C₀₋₆alkylcarbonyl C₀₋₆alkyl, (31) C₁₋₆alkylcarbonyloxy, (32) aryl C₀₋₆alkylcarbonyloxy, (33) C₁₋₆ alkylcarbonylamino, (34) aryl C₀₋₆ alkylcarbonylamino, (35) C₁₋₆alkylsulfonylamino, (36) aryl C₀₋₆alkylsulfonylamino, (37) C₁₋₆alkoxycarbonylamino, (38) aryl C₀₋₆ alkoxycarbonylamino, (39)C₁₋₆alkylaminocarbonylamino, (40) aryl C₀₋₆alkylaminocarbonylamino, (41)(C₁₋₆alkyl)₂ aminocarbonylamino, (42) (aryl C₀₋₆alkyl)₂aminocarbonylamino, (43) (C₁₋₆alkyl)₂ aminocarbonyloxy, and (44) (arylC₀₋₆alkyl)₂ aminocarbonyloxy; or, R⁴ and R⁵ together form an oxo groupor ═CH—R⁶ or a spiro C₃₋₇ cycloalkyl ring, unsubstituted or substitutedwith R⁶; R⁶ is selected from: (1) hydrogen, and (2) C₁₋₄ alkyl; or apharmaceutically acceptable salt thereof. for the preparation of amedicament useful treating a condition which is caused by androgendeficiency or which can be ameliorated by androgen administrationselected from: osteoporosis, periodontal disease, bone fracture, bonedamage following bone reconstructive surgery, sarcopenia, frailty, agingskin, male hypogonadism, post-menopausal symptoms in women,atherosclerosis, hypercholesterolemia, hyperlipidemia, aplastic anemiaand other hematopoietic disorders, pancreatic cancer, renal cancer,arthritis and joint repair, in a patient in need of such treatment.